Organic light-emitting device, host material, light-emitting material, and compound

ABSTRACT

A high light emission efficiency can be achieved by the use of a compound represented by the general formula (1) as a host material or a light-emitting material of a light-emitting layer of an organic light-emitting device. X 1  to X 12  each independently represent C or BH constituting carborane, provided that among X 1  to X 12 , the bonding positions to A and D each represent C, and the other thereof each represent BH; A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

TECHNICAL FIELD

The present invention relates to a compound that is useful as a host material and the like, and an organic light-emitting device using the same.

BACKGROUND ART

An organic light-emitting device, such as an organic electroluminescent device (organic EL device), has been actively studied for enhancing the light emission efficiency thereof. In particular, various studies for enhancing the light-emitting efficiency have been made by newly developing and combining an electron transporting material, a hole transporting material, a light-emitting material, a host material, and the like constituting an organic electroluminescent device. Among these, there are studies relating to an organic electroluminescent device utilizing a compound having a carborane structure.

Non-patent Document 1 describes the results of studies on the characteristics as a host material for blue phosphorescence of a carborane derivative represented by the following formula and a compound having a carbazolylphenyl group bonded to an o-position or a p-position of a carborane structure. However, the compounds described in Non-patent Document 1 are all symmetric molecules having the groups bonded to the carborane structure that are the same as each other, and a compound having different groups that are bonded to a carborane structure is not described.

Patent Document 1 describes a carborane derivative having silyl groups bonded thereto represented, for example, by the following formula and a compound having a silyl group and another group bonded to a carborane structure, and describes an example using the carborane derivative as a host material in a light-emitting layer present between a pair of electrodes constituting an organic electroluminescent device. However, the carborane derivatives shown in Patent Document 1 are all compounds having a silyl group bonded to a carborane structure, and the literature does not describe a carborane derivative having combined therewith a group other than a silyl group.

Patent Document 2 describes the usefulness of a carborane derivative represented by the following general formula as a material for an electron transporting layer of an organic electroluminescent device. In the formula herein, it is stated that R¹ to R⁸ each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted condensed polycyclic heterocyclic group, and compounds, in which R¹ and R⁸ are carbazolylphenyl groups, are described as specific examples thereof. However, Patent Document 2 does not confirm the usefulness of the carborane derivative represented by the following general formula as a host material and a light-emitting material.

CITATION LIST Non-Patent Literature

-   Non-patent Document 1: J. Am. Chem. Soc. 2012, 134, 17982-17990

Patent Literatures

-   Patent Document 1: WO 2013/088934 -   Patent Document 2: JP-A-2005-166574

SUMMARY OF INVENTION Technical Problem

As described above, Non-patent Document 1 describes the results of studies on the characteristics as a host material of the compound having two carbazolylphenyl groups bonded to the carborane structure. However, as a result of actual evaluation by the present inventors of the characteristics as a host material of the compound having two carbazolylphenyl groups bonded to the carborane structure, it has been found that the characteristics are not sufficiently satisfactory, and there is a demand of providing a host material having better characteristics.

The inventors then start to investigate variously a group of compounds having a carborane structure, have firstly found that among many compounds having a carborane structure, a group of compounds having a structure containing a carborane structure having an acceptor and a donor bonded thereto has usefulness as a host material and the like, and have decided to continue further investigations. As described above, Patent Document 1 describes an example using the compound containing a carborane structure having silyl groups bonded thereto as a host material of a light-emitting layer. However, a silyl group does not function as an acceptor or a donor, and Patent Document 1 does not describe a compound containing a carborane structure having an acceptor and a donor bonded thereto. Patent Document 2 describes the usefulness of a compound containing a carborane structure having two carbazolylphenyl groups bonded thereto as a material for an electron transporting layer, and furthermore Non-patent Document 1 describes the result of investigations on the characteristics of the compound as a host material. Herein, a carbazolylphenyl group functions as a donor. However, Patent Document 1 and Non-patent Document 1 do not describe a compound containing a carborane structure having both a donor and an acceptor bonded thereto. Accordingly, for a compound containing a carborane structure having an acceptor and a donor bonded thereto, the usefulness as a host material, and the like of the compound cannot be estimated.

Under the circumstances, the inventors have further made investigations on the usefulness as a host material and the like of a compound containing a carborane structure having an acceptor and a donor bonded thereto, and have made accumulated studies for finding a compound having excellent characteristics as a host material and the like. Furthermore, the inventors have made earnest investigations for providing a general formula of compounds useful as a host material and generalizing the structure of an organic light-emitting material having a high light emission efficiency.

Solution to Problem

As a result of the earnest investigations performed, the inventors have found that compounds containing a carborane structure having an acceptor and a donor bonded thereto through an aromatic ring or a heteroaromatic ring has excellent properties as a host material and the like. The inventors also have found that the group of compounds includes compounds that are useful as a light-emitting material, such as a delayed fluorescent material, and have clarified that an organic light-emitting device having a high light emission efficiency can be provided inexpensively. Based on the knowledge, the inventors have provided the following inventions as measures for solving the problems.

[1] An organic light-emitting device containing a compound represented by the following general formula (1):

wherein in the general formula (1), X¹ to X¹² each independently represent C or BH constituting carborane, provided that among X¹ to X¹², the bonding positions to A and D each represent C, and the other thereof each represent BH; A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

[2] The organic light-emitting device according to the item [1], wherein the organic light-emitting device contains the compound represented by the general formula (1) in a light-emitting layer.

[3] The organic light-emitting device according to the item [2], wherein the organic light-emitting device contains the compound represented by the general formula (1) as a host material.

[4] The organic light-emitting device according to the item [3], wherein the light-emitting layer further contains a delayed fluorescent emitter.

[5] The organic light-emitting device according to the item [2], wherein the organic light-emitting device contains the compound represented by the general formula (1) as a light-emitting material.

[6] The organic light-emitting device according to any one of the items [1] to [5], wherein in the general formula (1), D is bonded to the carborane through a benzene ring.

[7] The organic light-emitting device according to any one of the items [1] to [6], wherein in the general formula (1), D has a diphenylamino group or a carbazolyl group.

[8] The organic light-emitting device according to any one of the items [1] to [7], wherein in the general formula (1), D represents a group represented by the following general formula (2): [(R¹)(R²)N]^(n1)—Ar¹—  General Formula (2) wherein in the general formula (2), R¹ and R² each independently represent a substituent, provided that R¹ and R² may be bonded to each other to form a cyclic structure; n1 represents an integer of from 1 to 4; and Ar¹ represents a substituted or unsubstituted aromatic group having a valence of (n1+1).

[9] The organic light-emitting device according to the item [8], wherein in the general formula (2), n1 represents 1 or 2.

[10] The organic light-emitting device according to any one of the items [1] to [9], wherein in the general formula (1), A has a heteroaromatic ring containing a nitrogen atom.

[11] The organic light-emitting device according to the item [10], wherein in the general formula (1), A has a triazine ring.

[12] The organic light-emitting device according to the item [11], wherein the triazine ring is substituted with a phenyl group.

[13] The organic light-emitting device according to any one of the items [10] to [12], wherein in the general formula (1), A is bonded to the carborane through the heteroaromatic ring containing a nitrogen atom.

[14] The organic light-emitting device according to any one of the items [10] to [12], wherein in the general formula (1), A represents a group represented by the following general formula (3): (Het)_(n2)-Ar²—  General Formula (3) wherein in the general formula (3), Het represents a substituted or unsubstituted heteroaromatic ring group (provided that the heteroaromatic ring group contains a nitrogen atom as a ring structure constituting atom); n2 represents an integer of from 1 to 4; and Ar² represents a substituted or unsubstituted aromatic group having a valence of (n2+1).

[15] The organic light-emitting device according to the item [14], wherein in the general formula (3), n2 represents 1 or 2.

[16] The organic light-emitting device according to any one of the items [1] to [15], wherein the compound represented by the general formula (1) is an o-carborane compound or a m-carborane compound.

[17] The organic light-emitting device according to any one of the items [1] to [16], wherein the organic light-emitting device is an organic electroluminescent device.

[18] The organic light-emitting device according to any one of the items [1] to [17], wherein the organic light-emitting device emits delayed fluorescent light.

[19] A host material containing a compound represented by the following general formula (1):

wherein in the general formula (1), X¹ to X¹² each independently represent C or BH constituting carborane, provided that among X¹ to X¹², the bonding positions to A and D each represent C, and the other thereof each represent BH; A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

[20] A light-emitting material containing a compound represented by the following general formula (1):

wherein in the general formula (1), X¹ to X¹² each independently represent C or BH constituting carborane, provided that among X¹ to X¹², the bonding positions to A and D each represent C, and the other thereof each represent BH; A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

[21] A delayed fluorescent emitter containing a compound represented by the following general formula (1):

wherein in the general formula (1), X¹ to X¹² each independently represent C or BH constituting carborane, provided that among X¹ to X¹², the bonding positions to A and D each represent C, and the other thereof each represent BH; A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

[22] A compound represented by the following general formula (1′):

wherein in the general formula (1′), X^(1′) to X^(12′) each independently represent C or BH constituting carborane, provided that among X^(1′) to X^(12′), the bonding positions to A′ and D′ each represent C, and the other thereof each represent BH; A′ represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D′ represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

Advantageous Effects of Invention

The compound represented by the general formula (1) is useful as a host material and/or a light-emitting material. The compound of the invention includes one that emits delayed fluorescent light. The organic light-emitting device using the compound of the invention as a host material or a light-emitting material is capable of achieving a high light emission efficiency.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 shows a schematic cross sectional view showing an example of a layer structure of an organic electroluminescent device.

FIG. 2 shows the light emission and absorption spectra of the thin film organic photoluminescent device of 4CzIPN and the compound 1 in Example 1.

FIG. 3 shows the light emission spectrum of the organic electroluminescent device of 4CzIPN and the compound 1 in Example 2.

FIG. 4 is a graph showing the voltage-current density-luminance characteristics of the organic electroluminescent device of 4CzIPN and the compound 1 in Example 2.

FIG. 5 is a graph showing the current density-external quantum efficiency characteristics of the organic electroluminescent device of 4CzIPN and the compound 1 in Example 2.

FIG. 6 shows the light emission and absorption spectra of the toluene solutions before bubbling with nitrogen and the thin film organic photoluminescent device of the compound 1 in Example 3.

FIG. 7 shows the light emission and absorption spectra of the toluene solutions after bubbling with nitrogen and the thin film organic photoluminescent device of the compound 1 in Example 3.

FIG. 8 shows the light emission spectra for fluorescent light, delayed fluorescent light, and total fluorescent light of the organic photoluminescent device of the compound 1 in Example 3.

FIG. 9 shows the transient decay curve of the organic photoluminescent device of the compound 1 in Example 3.

FIG. 10 shows the light emission and absorption spectra of the toluene solution of the compound 2 in Example 4.

DESCRIPTION OF EMBODIMENTS

The contents of the invention will be described in detail below. The constitutional elements may be described below with reference to representative embodiments and specific examples of the invention, but the invention is not limited to the embodiments and the examples. In the description, a numerical range expressed with reference to an upper limit and/or a lower limit means a range that includes the upper limit and/or the lower limit. In the invention, the hydrogen atom that is present in a molecule of the compound used in the invention is not particularly limited in isotope species, and for example, all the hydrogen atoms in the molecule may be ¹H, and all or a part of them may be ²H (deuterium (D)).

Compound represented by General Formula (1)

The organic light-emitting device of the invention contains a compound represented by the following general formula (1).

In the general formula (1), X¹ to X¹² each independently represent C or BH constituting carborane, provided that among X¹ to X¹², the bonding positions to A and D each represent C, and the other thereof each represent BH. Among X¹ to X¹², the bonding positions to A and D may be any of X¹ to X¹², and in the case where any one of A and D is bonded to X¹, the other thereof is preferably bonded to X² or X³. Accordingly, the compound represented by the general formula (1) is preferably an o-carborane compound or a m-carborane compound. Among X¹ to X¹², BH may have a substituent substituting the hydrogen atom. For the descriptions and the preferred ranges of the substituent capable of being substituted on X¹ to X¹², reference may be made to the descriptions and the preferred ranges of the substituent that may be represented by R¹ and R² described later.

D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring. The “donor” referred in the invention means an aromatic substituent having an electron donating function to the carborane.

The donor represented by D has at least one aromatic ring or heteroaromatic ring, and is bonded to the carborane through the aromatic ring or heteroaromatic ring. Examples of the aromatic ring and the heteroaromatic ring include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a triazole ring, a thiazole ring, and a pyrrole ring, and the donor is preferably bonded to the carborane through a benzene ring among these. The bonding position to the carborane in the aromatic ring or the heteroaromatic ring is not particularly limited, and the donor is preferably bonded to the carborane at a carbon atom among the atoms constituting the aromatic ring or the heteroaromatic ring.

D preferably has a diphenylamino group or a carbazolyl group. The diphenylamino group and the carbazolyl group may be substituted with a substituent. For the descriptions and the preferred ranges of the substituent capable of being substituted on the diphenylamino group and the carbazolyl group, reference may be made to the descriptions and the preferred ranges of the substituent that may be represented by R¹ and R².

D is also preferably a group represented by the following general formula (2). [(R¹)(R²)N]^(n1)—Ar¹—  General Formula (2) In the general formula (2), R¹ and R² each independently represent a substituent.

Examples of the substituent that may be represented by R¹ and R² include a hydroxy group, a halogen atom, a cyano group, an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, an alkylthio group having from 1 to 20 carbon atoms, an alkyl-substituted amino group having from 1 to 20 carbon atoms, an acyl group having from 2 to 20 carbon atoms, an aryl group having from 6 to 40 carbon atoms, a heteroaryl group having from 3 to 40 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an alkynyl group having from 2 to 10 carbon atoms, an alkoxycarbonyl group having from 2 to 10 carbon atoms, an alkylsulfonyl group having from 1 to 10 carbon atoms, a haloalkyl group having from 1 to 10 carbon atoms, an amide group, an alkylamide group having from 2 to 10 carbon atoms, a trialkylsilyl group having from 3 to 20 carbon atoms, a trialkylsilylalkyl group having from 4 to 20 carbon atoms, a trialkylsilylalkenyl group having from 5 to 20 carbon atoms, a trialkylsilylalkynyl group having from 5 to 20 carbon atoms, and a nitro group. In these specific examples, the substituent that is capable of being further substituted with a substituent may be substituted. More preferred examples of the substituent include a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 40 carbon atoms, and a dialkyl-substituted amino group having from 1 to 20 carbon atoms. Further preferred examples of the substituent include a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having from 3 to 12 carbon atoms.

R¹ and R² may be bonded to each other to form a cyclic structure. The cyclic structure may be an aromatic ring or an aliphatic ring, and may be a structure containing a hetero atom, and the cyclic structure may be a condensed ring containing two or more rings. The hetero atom referred herein is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the cyclic structure formed include a benzene ring, a naphthalene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentaene ring, a cycloheptatriene ring, a cycloheptadiene ring, and a cycloheptaene ring.

n1 represents an integer of from 1 to 4, and preferably 1 or 2. In the case where n1 is an integer of from 2 to 4, the plural groups represented by [(R¹)(R²)N] may be the same as or different from each other.

Ar¹ represents a substituted or unsubstituted aromatic group having a valence of (n1+1). The aromatic group referred herein includes a monocyclic aromatic group and also includes an aromatic group having a ring aggregated structure containing two or more aromatic rings bonded through a single bond, such as biphenylene, and an aromatic group having a polycyclic condensed structure containing two or more aromatic rings condensed, such as naphthalene. Specifically, the aromatic group is preferably an aromatic hydrocarbon group having from 6 to 18 carbon atoms, more preferably a residual group of a benzene ring, a biphenylene ring, a naphthalene ring, a fluorene ring, or a triphenylene ring, further preferably a residual group of a benzene ring, and still further preferably a divalent residual group of a benzene ring having bonding positions at the 1-position and the 4-position (i.e., a 1,4-phenylene group). The aromatic group may be substituted with a substituent. For the descriptions and the preferred ranges of the substituent capable of being substituted on the aromatic group, reference may be made to the descriptions and the preferred ranges of the substituent that may be represented by R¹ and R² above.

A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring. The “acceptor” referred in the invention means an aromatic substituent having an electron withdrawing function to the carborane.

The acceptor represented by A has at least one aromatic ring or heteroaromatic ring, and is bonded to the carborane through the aromatic ring or heteroaromatic ring. For the specific examples of the aromatic ring and the heteroaromatic ring, reference may be made to the specific examples of the aromatic ring and the heteroaromatic ring of the donor bonded to the carborane. The bonding position to the carborane in the aromatic ring or the heteroaromatic ring is not particularly limited, and the acceptor is preferably bonded to the carborane at a carbon atom among the atoms constituting the aromatic ring or the heteroaromatic ring.

A preferably has a heteroaromatic ring containing a nitrogen atom. Examples of the heteroaromatic ring containing a nitrogen atom include a pyridine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a triazole ring, a thiazole ring, and a pyrrole ring, and a triazine ring is preferred. The heteroaromatic ring containing a nitrogen atom may be substituted with a substituent. For the descriptions and the preferred ranges of the substituent capable of being substituted on the heteroaromatic ring containing a nitrogen atom, reference may be made to the descriptions and the preferred ranges of the substituent that may be represented by R¹ and R² above. In the case where the heteroaromatic ring containing a nitrogen atom is a triazine ring, the triazine ring is preferably substituted with a phenyl group. In the case where A has a heteroaromatic ring containing a nitrogen atom, the heteroaromatic ring containing a nitrogen atom may be bonded to the carborane through a single bond, or may be bonded to the carborane through an aromatic group Ar² as a linking group, as represented by the following general formula (3). (Het)_(n2)-Ar²—  General Formula (3)

In the general formula (3), Het represents a substituted or unsubstituted heteroaromatic ring group (provided that the heteroaromatic ring group contains a nitrogen atom as a ring structure constituting atom). Examples of the heteroaromatic ring group containing a nitrogen atom include residual groups of a pyridine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a triazole ring, a thiazole ring, and a pyrrole ring, and a residual group of a triazine ring is preferred. In the case where the heteroaromatic ring group has a substituent, for the descriptions and the preferred ranges of the substituent, reference may be made to the descriptions and the preferred ranges of the substituent that may be represented by R¹ and R² above. In the case where the heteroaromatic ring group containing a nitrogen atom is a residual group of a triazine ring, the residual group of a triazine ring is preferably substituted with a phenyl group.

n2 represents an integer of from 1 to 4, and preferably 1 or 2. In the case where n2 is an integer of from 2 to 4, the plural groups represented by Het may be the same as or different from each other.

Ar² represents a substituted or unsubstituted aromatic group having a valence of (n2+1). For the descriptions and the preferred ranges of the aromatic group represented by Ar², reference may be made to the descriptions and the preferred examples of the aromatic group represented by Ar¹.

Preferred examples of the compound represented by the general formula (1) include a compound having a structure containing a m-carborane or an o-carborane having bonded thereto a donor D having a carbazole ring and an acceptor A having a triazine ring, and more preferred examples of the compound include a compound having a structure containing a m-carborane or an o-carborane having bonded thereto a donor D having a carbazole ring and an acceptor A having a triazine ring, in which at least the carbazole ring of D is bonded to the carborane through a phenylene ring.

Specific examples of the compound represented by the general formula (1) are shown below. However, the compound represented by the general formula (1) capable of being used in the invention is not construed as being limited to the specific examples.

The molecular weight of the compound represented by the general formula (1) is preferably 1,500 or less, more preferably 1,200 or less, and further preferably 1,000 or less, for example, in the case where an organic layer containing the compound represented by the general formula (1) is intended to be formed as a film by a vapor deposition method. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1).

The compound represented by the general formula (1) may be formed into a film by a coating method irrespective of the molecular weight thereof. The compound that has a relatively large molecular weight may be formed into a film by a coating method.

As an application of the invention, it may be considered that a compound that contains plural structures each represented by the general formula (1) in the molecule is used as a host material or a light-emitting material.

For example, it may be considered that a polymerizable group is introduced in advance to the structure represented by the general formula (1), and a polymer obtained by polymerizing the polymerizable group is used as a light-emitting material. Specifically, it may be considered that a monomer that has a polymerizable functional group at any of X¹ to X¹², A, and D in the general formula (1) is prepared, and is homopolymerized or copolymerized with another monomer to prepare a polymer containing repeating units, and the polymer is used as a host material or a light-emitting material. In alternative, it may be considered that the compounds represented by the general formula (1) are reacted to form a dimer or a trimer, and the dimer or the trimer is used as a light-emitting material.

Examples of the polymer having the repeating unit containing the structure represented by the general formula (1) include a polymer containing a structure represented by the following general formula (4) or (5).

In the general formulae (4) and (5), Q represents a group containing the structure represented by the general formula (1), and L¹ and L² each represent a linking group. The linking group preferably has from 0 to 20 carbon atoms, more preferably from 1 to 15 carbon atoms, and further preferably from 2 to 10 carbon atoms. The linking group preferably has a structure represented by —X¹⁰¹-L¹¹-, wherein X¹⁰¹ represents an oxygen atom or a sulfur atom, and preferably an oxygen atom, and L¹¹ represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having from 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

In the general formulae (4) and (5), R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ each independently represent a substituent, preferably a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having from 1 to 3 carbon atoms, an unsubstituted alkoxy group having from 1 to 3 carbon atoms, a fluorine atom or a chlorine atom, and further preferably an unsubstituted alkyl group having from 1 to 3 carbon atoms or an unsubstituted alkoxy group having from 1 to 3 carbon atoms.

The linking group represented by L¹ and L² may be bonded to any of X¹ to X¹², A, and D of the structure of the general formula (1), any of R¹, R², and Ar¹ of the structure of the general formula (2), and any of Het and Ar² of the structure of the general formula (3), constituting Q. Two or more of the linking groups may be boded to one group represented by Q to form a crosslinked structure or a network structure.

Specific examples of the structure of the repeating unit include structures represented by the following formulae (6) to (9).

The polymer having the repeating unit containing the structure represented by any of the formulae (6) to (9) may be synthesized in such a manner that a hydroxy group is introduced to any of X¹ to X¹², A, and D in the structure represented by the general formula (1), and the hydroxy group as a linker is reacted with the following compound to introduce a polymerizable group thereto, followed by polymerizing the polymerizable group.

The polymer containing the structure represented by the general formula (1) in the molecule may be a polymer containing only a repeating unit having the structure represented by the general formula (1), or a polymer further containing a repeating unit having another structure. The repeating unit having the structure represented by the general formula (1) contained in the polymer may be only one kind or two or more kinds. Examples of the repeating unit that does not have the structure represented by the general formula (1) include a repeating unit derived from a monomer that is used for ordinary copolymerization. Examples of the repeating unit include a repeating unit derived from a monomer having an ethylenic unsaturated bond, such as ethylene and styrene.

Compound Represented by General Formula (1′)

The compound represented by the general formula (1′) is a novel compound.

In the general formula (1′), X^(1′) to X^(12′) each independently represent C or BH constituting carborane, provided that among X^(1′) to X^(12′), the bonding positions to A′ and D′ each represent C, and the other thereof each represent BH; A′ represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D′ represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring.

For the descriptions and the preferred ranges of X^(1′) to X^(12′), A′, and D′, reference may be made to the descriptions of the compound represented by the general formula (1).

Synthesis Method of Compound Represented by General Formula (1′)

The compound represented by the general formula (1′) may be synthesized by combining the known reactions. For example, a compound represented by the general formula (1′), in which X^(1′) represents a group represented by the general formula (3), X^(3′) represents a group represented by the general formula (2), and Ar¹ and Ar² each represent a phenylene group, can be synthesized by reacting the following two compounds.

For the descriptions of R¹, R², Het, n1, and n2 in the aforementioned reaction scheme, reference may be made to the corresponding descriptions in the general formulae (2) and (3). X represents a halogen atom, examples of which include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom, a bromine atom, and an iodine atom are preferred.

The reactions in the aforementioned scheme each are an application of the known reactions, and the known reaction conditions may be appropriately selected and used. For the details of the reactions, reference may be made to the synthesis examples described later. The compound represented by the general formula (1′) may also be synthesized by combining the other known synthesis reactions.

Organic Light-Emitting Device

The compound represented by the general formula (1) of the invention is useful as a host material and/or a light-emitting material of an organic light-emitting device. Accordingly, the compound represented by the general formula (1) of the invention may be effectively used as a host material or a light-emitting material in a light-emitting layer of an organic light-emitting device. The compound represented by the general formula (1) includes a delayed fluorescent emitter emitting delayed fluorescent light. Thus, the invention provides an invention relating to a delayed fluorescent emitter having the structure represented by the general formula (1), an invention relating to the use of the compound represented by the general formula (1) as the delayed fluorescent emitter, and an invention relating to a method for emitting delayed fluorescent light with the compound represented by the general formula (1). An organic light-emitting device that uses the compound as a light-emitting material has features that the device emits delayed fluorescent light and has a high light emission efficiency. The principle of the features may be described as follows for an organic electroluminescent device as an example.

In an organic electroluminescent device, carriers are injected from an anode and a cathode to a light-emitting material to form an excited state for the light-emitting material, with which light is emitted. In the case of a carrier injection type organic electroluminescent device, in general, excitons that are excited to the excited singlet state are 25% of the total excitons generated, and the remaining 75% thereof are excited to the excited triplet state. Accordingly, the use of phosphorescence, which is light emission from the excited triplet state, provides a high energy utilization. However, the excited triplet state has a long lifetime and thus causes saturation of the excited state and deactivation of energy through mutual action with the excitons in the excited triplet state, and therefore the quantum yield of phosphorescence may generally be often not high. A delayed fluorescent material emits fluorescent light through the mechanism that the energy of excitons transits to the excited triplet state through intersystem crossing or the like, and then transits to the excited singlet state through reverse intersystem crossing due to triplet-triplet annihilation or absorption of thermal energy, thereby emitting fluorescent light. It is considered that among the materials, a thermal activation type delayed fluorescent material emitting light through absorption of thermal energy is particularly useful for an organic electroluminescent device. In the case where a delayed fluorescent material is used in an organic electroluminescent device, the excitons in the excited singlet state normally emit fluorescent light. On the other hand, the excitons in the excited triplet state emit fluorescent light through intersystem crossing to the excited singlet state by absorbing the heat generated by the device. At this time, the light emitted through reverse intersystem crossing from the excited triplet state to the excited singlet state has the same wavelength as fluorescent light since it is light emission from the excited singlet state, but has a longer lifetime (light emission lifetime) than the normal fluorescent light and phosphorescent light, and thus the light is observed as fluorescent light that is delayed from the normal fluorescent light and phosphorescent light. The light may be defined as delayed fluorescent light. The use of the thermal activation type exciton transition mechanism may raise the proportion of the compound in the excited singlet state, which is generally formed in a proportion only of 25%, to 25% or more through the absorption of the thermal energy after the carrier injection. A compound that emits strong fluorescent light and delayed fluorescent light at a low temperature of lower than 100° C. undergoes the intersystem crossing from the excited triplet state to the excited singlet state sufficiently with the heat of the device, thereby emitting delayed fluorescent light, and thus the use of the compound may drastically enhance the light emission efficiency.

The use of the compound represented by the general formula (1) of the invention as a host material or a light-emitting material of a light-emitting layer may provide an excellent organic light-emitting device, such as an organic photoluminescent device (organic PL device) and an organic electroluminescent device (organic EL device). At this time, the compound represented by the general formula (1) of the invention may have a function of assisting light emission of another light-emitting material contained in the light-emitting layer, i.e., as a so-called assist dopant. Specifically, the compound represented by the general formula (1) of the invention contained in the light-emitting layer may have a lowest excited singlet energy level that is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the another light-emitting material contained in the light-emitting layer.

The organic photoluminescent device has a structure containing a substrate having formed thereon at least a light-emitting layer. The organic electroluminescent device has a structure containing at least an anode, a cathode and an organic layer formed between the anode and the cathode. The organic layer contains at least a light-emitting layer, and may be formed only of a light-emitting layer, or may have one or more organic layer in addition to the light-emitting layer. Examples of the organic layer include a hole transporting layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transporting layer and an exciton barrier layer. The hole transporting layer may be a hole injection and transporting layer having a hole injection function, and the electron transporting layer may be an electron injection and transporting layer having an electron injection function. A specific structural example of an organic electroluminescent device is shown in FIG. 1. In FIG. 1, the numeral 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a hole transporting layer, 5 denotes a light-emitting layer, 6 denotes an electron transporting layer, and 7 denotes a cathode.

The members and the layers of the organic electroluminescent device will be described below. The descriptions for the substrate and the light-emitting layer may also be applied to the substrate and the light-emitting layer of the organic photoluminescent device.

Substrate

The organic electroluminescent device of the invention is preferably supported by a substrate. The substrate is not particularly limited and may be those that have been commonly used in an organic electroluminescent device, and examples thereof used include those formed of glass, transparent plastics, quartz and silicon.

Anode

The anode of the organic electroluminescent device used is preferably formed of as an electrode material a metal, an alloy or an electroconductive compound each having a large work function (4 eV or more), or a mixture thereof. Specific examples of the electrode material include a metal, such as Au, and an electroconductive transparent material, such as CuI, indium tin oxide (ITO), SnO₂ and ZnO. A material that is amorphous and is capable of forming a transparent electroconductive film, such as IDIXO (In₂O₃—ZnO), may also be used. The anode may be formed in such a manner that the electrode material is formed into a thin film by such a method as vapor deposition or sputtering, and the film is patterned into a desired pattern by a photolithography method, or in the case where the pattern may not require high accuracy (for example, approximately 100 μm or more), the pattern may be formed with a mask having a desired shape on vapor deposition or sputtering of the electrode material. In alternative, in the case where a material capable of being applied as a coating, such as an organic electroconductive compound, is used, a wet film forming method, such as a printing method and a coating method, may be used. In the case where emitted light is to be taken out through the anode, the anode preferably has a transmittance of more than 10%, and the anode preferably has a sheet resistance of several hundred Ohm per square or less. The thickness thereof may be generally selected from a range of from 10 to 1,000 nm, and preferably from 10 to 200 nm, while depending on the material used.

Cathode

The cathode is preferably formed of as an electrode material a metal having a small work function (4 eV or less) (referred to as an electron injection metal), an alloy or an electroconductive compound each having a small work function (4 eV or less), or a mixture thereof. Specific examples of the electrode material include sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-copper mixture, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminum mixture, and a rare earth metal. Among these, a mixture of an electron injection metal and a second metal that is a stable metal having a larger work function than the electron injection metal, for example, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture, a lithium-aluminum mixture, and aluminum, are preferred from the standpoint of the electron injection property and the durability against oxidation and the like. The cathode may be produced by forming the electrode material into a thin film by such a method as vapor deposition or sputtering. The cathode preferably has a sheet resistance of several hundred Ohm per square or less, and the thickness thereof may be generally selected from a range of from 10 nm to 5 μm, and preferably from 50 to 200 nm. For transmitting the emitted light, any one of the anode and the cathode of the organic electroluminescent device is preferably transparent or translucent, thereby enhancing the light emission luminance.

The cathode may be formed with the electroconductive transparent materials described for the anode, thereby forming a transparent or translucent cathode, and by applying the cathode, a device having an anode and a cathode, both of which have transmittance, may be produced.

Light-Emitting Layer

The light-emitting layer is a layer, in which holes and electrons injected from the anode and the cathode, respectively, are recombined to form excitons, and then the layer emits light. A light-emitting material may be solely used as the light-emitting layer, but the light-emitting layer preferably contains a light-emitting material and a host material.

In the case where the compound represented by the general formula (1) as a host material, one kind or two or more kinds selected from a group of compounds represented by the general formula (1) may be used. The light-emitting material may be a fluorescent light-emitting material or may be a phosphorescent light-emitting material, and in the case using a fluorescent light-emitting material, the light-emitting material is preferably one that emits delayed fluorescent light. A high light emission efficiency can be obtained thereby. In order that the organic electroluminescent device and the organic photoluminescent device of the invention exhibit a high light emission efficiency, it is important that the singlet excitons and the triplet excitons generated in the light-emitting material are confined in the light-emitting material. Accordingly, the light-emitting material combined with the compound represented by the general formula (1) is preferably a compound that has excited singlet energy and excited triplet energy, at least one of which is higher than those of the compound represented by the general formula (1). As a result, the singlet excitons and the triplet excitons generated in the light-emitting material of the invention are capable of being confined in the molecules of the light-emitting material, thereby eliciting the light emission efficiency thereof sufficiently.

Examples of the light-emitting material combined with a host material containing the compound represented by the general formula (1) include a light-emitting material capable of emitting delayed fluorescent light. Preferred examples of the light-emitting material will be described below, but the light-emitting material capable of being used in the invention is not limited to the following examples.

Preferred examples of the light-emitting material include compounds represented by the following general formula (101). The entire description of WO 2013/154064 including the paragraphs 0008 to 0048 and 0095 to 0133 is incorporated herein by reference.

wherein in the general formula (101), at least one of R¹ to R⁵ represents a cyano group, at least one of R¹ to R⁵ represents a group represented by the following general formula (111), and the balance of R¹ to R⁵ each represent a hydrogen atom or a substituent,

wherein in the general formula (111), R²¹ to R²⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of the following conditions (A) and (B) is satisfied:

(A) R²⁵ and R²⁶ together form a single bond, and

(B) R²⁷ and R²⁸ together represent an atomic group that is necessary for forming a substituted or unsubstituted benzene ring.

In the general formula (101), at least one of R¹ to R⁵ preferably represents a group represented by any one of the following general formulae (112) to (115).

wherein in the general formula (112), R³¹ to R³⁸ each independently represent a hydrogen atom or a substituent, General Formula (113)

wherein in the general formula (113), R⁴¹ to R⁴⁶ each independently represent a hydrogen atom or a substituent,

wherein in the general formula (114), R⁵¹ to R⁶² each independently represent a hydrogen atom or a substituent,

wherein in the general formula (115), R⁷¹ to R⁸⁰ each independently represent a hydrogen atom or a substituent.

Specific examples of the compounds include the compounds shown in the following tables. In the case where two or more groups represented by any one of the general formulae (112) to (115) are present in the molecule of the following example compounds, all the groups have the same structure. The formulae (121) to (124) in the tables represent the following formulae, respectively, and n represents the number of the repeating units.

TABLE 1 Compound General formula (1) General formula (112) No. R¹ R² R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 1 General General CN General General H H H H formula (112) formula (112) formula (112) formula (112) 2 General General CN General General H CH₃ H H formula (112) formula (112) formula (112) formula (112) 3 General General CN General General H CH₃O H H formula (112) formula (112) formula (112) formula (112) 4 General General CN General General H H CH₃ H formula (112) formula (112) formula (112) formula (112) 5 General General CN General General H H CH₃O H formula (112) formula (112) formula (112) formula (112) 6 General General CN General General H H t-C₄H₉ H formula (112) formula (112) formula (112) formula (112) 7 General General CN General General H H Cl H formula (112) formula (112) formula (112) formula (112) 8 General General CN General General H H F H formula (112) formula (112) formula (112) formula (112) 9 General General CN General General H H H CH₃ formula (112) formula (112) formula (112) formula (112) 10 General General CN General General H H H CH₃O formula (112) formula (112) formula (112) formula (112) 11 General General CN General H H H H H formula (112) formula (112) formula (112) 12 General General CN General H H CH₃ H H formula (112) formula (112) formula (112) 13 General General CN General H H CH₃O H H formula (112) formula (112) formula (112) 14 General General CN General H H H CH₃ H formula (112) formula (112) formula (112) 15 General General CN General H H H CH₃O H formula (112) formula (112) formula (112) 16 General General CN General H H H t-C₄H₉ H formula (112) formula (112) formula (112) 17 General General CN General H H H Cl H formula (112) formula (112) formula (112) 18 General General CN General H H H F H formula (112) formula (112) formula (112) 19 General General CN General H H H H CH₃ formula (112) formula (112) formula (112) 20 General General CN General H H H H CH₃O formula (112) formula (112) formula (112) 21 General General CN H H H H H H formula (112) formula (112) 22 General General CN H H H CH₃ H H formula (112) formula (112) 23 General General CN H H H CH₃O H H formula (112) formula (112) 24 General General CN H H H H CH₃ H formula (112) formula (112) 25 General General CN H H H H CH₃O H formula (112) formula (112) 26 General General CN H H H H t-C₄H₉ H formula (112) formula (112) 27 General General CN H H H H Cl H formula (112) formula (112) 28 General General CN H H H H F H formula (112) formula (112) 29 General General CN H H H H H CH₃ formula (112) formula (112) 30 General General CN H H H H H CH₃O formula (112) formula (112) 31 General H CN General H H H H H formula (112) formula (112) 32 General H CN General H H CH₃ H H formula (112) formula (112) 33 General H CN General H H CH₃O H H formula (112) formula (112) 34 General H CN General H H H CH₃ H formula (112) formula (112) 35 General H CN General H H H CH₃O H formula (112) formula (112) 36 General H CN General H H H t-C₄H₉ H formula (112) formula (112) 37 General H CN General H H H Cl H formula (112) formula (112) 38 General H CN General H H H F H formula (112) formula (112) 39 General H CN General H H H H CH₃ formula (112) formula (112) 40 General H CN General H H H H CH₃O formula (112) formula (112) 41 General H CN H General H H H H formula (112) formula (112) 42 General H CN H General H CH₃ H H formula (112) formula (112) 43 General H CN H General H CH₃O H H formula (112) formula (112) 44 General H CN H General H H CH₃ H formula (112) formula (112) 45 General H CN H General H H CH₃O H formula (112) formula (112) 46 General H CN H General H H t-C₄H₉ H formula (112) formula (112) 47 General H CN H General H H Cl H formula (112) formula (112) 48 General H CN H General H H F H formula (112) formula (112) 49 General H CN H General H H H CH₃ formula (112) formula (112) 50 General H CN H General H H H CH₃O formula (112) formula (112) 51 General H CN H H H H H H formula (112) 52 General H CN H H H CH₃ H H formula (112) 53 General H CN H H H CH₃O H H formula (112) 54 General H CN H H H H CH₃ H formula (112) 55 General H CN H H H H CH₃O H formula (112) 56 General H CN H H H H t-C₄H₉ H formula (112) 57 General H CN H H H H Cl H formula (112) 58 General H CN H H H H F H formula (112) 59 General H CN H H H H H CH₃ formula (112) 60 General H CN H H H H H CH₃O formula (112) 61 General General CN General F H H H H formula (112) formula (112) formula (112) 62 General General CN General F H CH₃ H H formula (112) formula (112) formula (112) 63 General General CN General F H CH₃O H H formula (112) formula (112) formula (112) 64 General General CN General F H H CH₃ H formula (112) formula (112) formula (112) 65 General General CN General F H H CH₃O H formula (112) formula (112) formula (112) 66 General General CN General F H H t-C₄H₉ H formula (112) formula (112) formula (112) 67 General General CN General F H H Cl H formula (112) formula (112) formula (112) 68 General General CN General F H H F H formula (112) formula (112) formula (112) 69 General General CN General F H H H CH₃ formula (112) formula (112) formula (112) 70 General General CN General F H H H CH₃O formula (112) formula (112) formula (112) 71 General General CN F F H H H H formula (112) formula (112) 72 General General CN F F H CH₃ H H formula (112) formula (112) 73 General General CN F F H CH₃O H H formula (112) formula (112) 74 General General CN F F H H CH₃ H formula (112) formula (112) 75 General General CN F F H H CH₃O H formula (112) formula (112) 76 General General CN F F H H t-C₄H₉ H formula (112) formula (112) 77 General General CN F F H H Cl H formula (112) formula (112) 78 General General CN F F H H F H formula (112) formula (112) 79 General General CN F F H H H CH₃ formula (112) formula (112) 80 General General CN F F H H H CH₃O formula (112) formula (112) 81 General F CN General F H H H H formula (112) formula (112) 82 General F CN General F H CH₃ H H formula (112) formula (112) 83 General F CN General F H CH₃O H H formula (112) formula (112) 84 General F CN General F H H CH₃ H formula (112) formula (112) 85 General F CN General F H H CH₃O H formula (112) formula (112) 86 General F CN General F H H t-C₄H₉ H formula (112) formula (112) 87 General F CN General F H H Cl H formula (112) formula (112) 88 General F CN General F H H F H formula (112) formula (112) 89 General F CN General F H H H CH₃ formula (112) formula (112) 90 General F CN General F H H H CH₃O formula (112) formula (112) 91 General F CN F General H H H H formula (112) formula (112) 92 General F CN F General H CH₃ H H formula (112) formula (112) 93 General F CN F General H CH₃O H H formula (112) formula (112) 94 General F CN F General H H CH₃ H formula (112) formula (112) 95 General F CN F General H H CH₃O H formula (112) formula (112) 96 General F CN F General H H t-C₄H₉ H formula (112) formula (112) 97 General F CN F General H H Cl H formula (112) formula (112) 98 General F CN F General H H F H formula (112) formula (112) 99 General F CN F General H H H CH₃ formula (112) formula (112) 100 General F CN F General H H H CH₃O formula (112) formula (112) 101 General F CN F F H H H H formula (112) 102 General F CN F F H CH₃ H H formula (112) 103 General F CN F F H CH₃O H H formula (112) 104 General F CN F F H H CH₃ H formula (112) 105 General F CN F F H H CH₃O H formula (112) 106 General F CN F F H H t-C₄H₉ H formula (112) 107 General F CN F F H H Cl H formula (112) 108 General F CN F F H H F H formula (112) 109 General F CN F F H H H CH₃ formula (112) 110 General F CN F F H H H CH₃O formula (112) 111 General General CN General OH H H H H formula (112) formula (112) formula (112) 112 General General CN General OH H CH₃ H H formula (112) formula (112) formula (112) 113 General General CN General OH H CH₃O H H formula (112) formula (112) formula (112) 114 General General CN General OH H H CH₃ H formula (112) formula (112) formula (112) 115 General General CN General OH H H CH₃O H formula (112) formula (112) formula (112) 116 General General CN General OH H H t-C₄H₉ H formula (112) formula (112) formula (112) 117 General General CN General OH H H Cl H formula (112) formula (112) formula (112) 118 General General CN General OH H H F H formula (112) formula (112) formula (112) 119 General General CN General OH H H H CH₃ formula (112) formula (112) formula (112) 120 General General CN General OH H H H CH₃O formula (112) formula (112) formula (112) 121 General General CN OH OH H H H H formula (112) formula (112) 122 General General CN OH OH H CH₃ H H formula (112) formula (112) 123 General General CN OH OH H CH₃O H H formula (112) formula (112) 124 General General CN OH OH H H CH₃ H formula (112) formula (112) 125 General General CN OH OH H H CH₃O H formula (112) formula (112) 126 General General CN OH OH H H t-C₄H₉ H formula (112) formula (112) 127 General General CN OH OH H H Cl H formula (112) formula (112) 128 General General CN OH OH H H F H formula (112) formula (112) 129 General General CN OH OH H H H CH₃ formula (112) formula (112) 130 General General CN OH OH H H H CH₃O formula (112) formula (112) 131 General OH CN General OH H H H H formula (112) formula (112) 132 General OH CN General OH H CH₃ H H formula (112) formula (112) 133 General OH CN General OH H CH₃O H H formula (112) formula (112) 134 General OH CN General OH H H CH₃ H formula (112) formula (112) 135 General OH CN General OH H H CH₃O H formula (112) formula (112) 136 General OH CN General OH H H t-C₄H₉ H formula (112) formula (112) 137 General OH CN General OH H H Cl H formula (112) formula (112) 138 General OH CN General OH H H F H formula (112) formula (112) 139 General OH CN General OH H H H CH₃ formula (112) formula (112) 140 General OH CN General OH H H H CH₃O formula (112) formula (112) 141 General OH CN OH General H H H H formula (112) formula (112) 142 General OH CN OH General H CH₃ H H formula (112) formula (112) 143 General OH CN OH General H CH₃O H H formula (112) formula (112) 144 General OH CN OH General H H CH₃ H formula (112) formula (112) 145 General OH CN OH General H H CH₃O H formula (112) formula (112) 146 General OH CN OH General H H t-C₄H₉ H formula (112) formula (112) 147 General OH CN OH General H H Cl H formula (112) formula (112) 148 General OH CN OH General H H F H formula (112) formula (112) 149 General OH CN OH General H H H CH₃ formula (112) formula (112) 150 General OH CN OH General H H H CH₃O formula (112) formula (112) 151 General OH CN OH OH H H H H formula (112) 152 General OH CN OH OH H CH₃ H H formula (112) 153 General OH CN OH OH H CH₃O H H formula (112) 154 General OH CN OH OH H H CH₃ H formula (112) 155 General OH CN OH OH H H CH₃O H formula (112) 156 General OH CN OH OH H H t-C₄H₉ H formula (112) 157 General OH CN OH OH H H Cl H formula (112) 158 General OH CN OH OH H H F H formula (112) 159 General OH CN OH OH H H H CH₃ formula (112) 160 General OH CN OH OH H H H CH₃O formula (112) 161 General General CN General Cl H H H H formula (112) formula (112) formula (112) 162 General General CN General Cl H CH₃ H H formula (112) formula (112) formula (112) 163 General General CN General Cl H CH₃O H H formula (112) formula (112) formula (112) 164 General General CN General Cl H H CH₃ H formula (112) formula (112) formula (112) 165 General General CN General Cl H H CH₃O H formula (112) formula (112) formula (112) 166 General General CN General Cl H H t-C₄H₉ H formula (112) formula (112) formula (112) 167 General General CN General Cl H H Cl H formula (112) formula (112) formula (112) 168 General General CN General Cl H H F H formula (112) formula (112) formula (112) 169 General General CN General Cl H H H CH₃ formula (112) formula (112) formula (112) 170 General General CN General Cl H H H CH₃O formula (112) formula (112) formula (112) 171 General General CN General F H H H H formula (112) formula (112) formula (112) 172 General General CN General F H CH₃ H H formula (112) formula (112) formula (112) 173 General General CN General F H CH₃O H H formula (112) formula (112) formula (112) 174 General General CN General F H H CH₃ H formula (112) formula (112) formula (112) 175 General General CN General F H H CH₃O H formula (112) formula (112) formula (112) 176 General General CN General F H H t-C₄H₉ H formula (112) formula (112) formula (112) 177 General General CN General F H H Cl H formula (112) formula (112) formula (112) 178 General General CN General F H H F H formula (112) formula (112) formula (112) 179 General General CN General F H H H CH₃ formula (112) formula (112) formula (112) 180 General General CN General F H H H CH₃O formula (112) formula (112) formula (112) 181 General General CN General CH₃O H H H H formula (112) formula (112) formula (112) 182 General General CN General CH₃O H CH₃ H H formula (112) formula (112) formula (112) 183 General General CN General CH₃O H CH₃O H H formula (112) formula (112) formula (112) 184 General General CN General CH₃O H H CH₃ H formula (112) formula (112) formula (112) 185 General General CN General CH₃O H H CH₃O H formula (112) formula (112) formula (112) 186 General General CN General CH₃O H H t-C₄H₉ H formula (112) formula (112) formula (112) 187 General General CN General CH₃O H H Cl H formula (112) formula (112) formula (112) 188 General General CN General CH₃O H H F H formula (112) formula (112) formula (112) 189 General General CN General C₂H₅O H H H CH₃ formula (112) formula (112) formula (112) 190 General General CN General C₂H₅O H H H CH₃O formula (112) formula (112) formula (112) 191 General General CN General C₂H₅O H H H H formula (112) formula (112) formula (112) 192 General General CN General C₂H₅O H CH₃ H H formula (112) formula (112) formula (112) 193 General General CN General C₂H₅O H CH₃O H H formula (112) formula (112) formula (112) 194 General General CN General C₂H₅O H H CH₃ H formula (112) formula (112) formula (112) 195 General General CN General C₂H₅O H H CH₃O H formula (112) formula (112) formula (112) 196 General General CN General C₂H₅O H H t-C₄H₉ H formula (112) formula (112) formula (112) 197 General General CN General C₂H₅O H H Cl H formula (112) formula (112) formula (112) 198 General General CN General C₂H₅O H H F H formula (112) formula (112) formula (112) 199 General General CN General C₂H₅O H H H CH₃ formula (112) formula (112) formula (112) 200 General General CN General C₂H₅O H H H CH₃O formula (112) formula (112) formula (112) 201 General General CN General C₆H₅O H H H H formula (112) formula (112) formula (112) 202 General General CN General C₆H₅O H CH₃ H H formula (112) formula (112) formula (112) 203 General General CN General C₆H₅O H CH₃O H H formula (112) formula (112) formula (112) 204 General General CN General C₆H₅O H H CH₃ H formula (112) formula (112) formula (112) 205 General General CN General C₆H₅O H H CH₃O H formula (112) formula (112) formula (112) 206 General General CN General C₆H₅O H H t-C₄H₉ H formula (112) formula (112) formula (112) 207 General General CN General C₆H₅O H H Cl H formula (112) formula (112) formula (112) 208 General General CN General C₆H₅O H H F H formula (112) formula (112) formula (112) 209 General General CN General C₆H₅O H H H CH₃ formula (112) formula (112) formula (112) 210 General General CN General C₆H₅O H H H CH₃O formula (112) formula (112) formula (112) 211 General General CN General Formula (121) H H H H formula (112) formula (112) formula (112) 212 General General CN General Formula (121) H CH₃ H H formula (112) formula (112) formula (112) 213 General General CN General Formula (121) H CH₃O H H formula (112) formula (112) formula (112) 214 General General CN General Formula (121) H H CH₃ H formula (112) formula (112) formula (112) 215 General General CN General Formula (121) H H CH₃O H formula (112) formula (112) formula (112) 216 General General CN General Formula (121) H H t-C₄H₉ H formula (112) formula (112) formula (112) 217 General General CN General Formula (121) H H Cl H formula (112) formula (112) formula (112) 218 General General CN General Formula (121) H H F H formula (112) formula (112) formula (112) 219 General General CN General Formula (121) H H H CH₃ formula (112) formula (112) formula (112) 220 General General CN General Formula (121) H H H CH₃O formula (112) formula (112) formula (112) 221 General General CN General Formula (122) H H H H formula (112) formula (112) formula (112) 222 General General CN General Formula (122) H CH₃ H H formula (112) formula (112) formula (112) 223 General General CN General Formula (122) H CH₃O H H formula (112) formula (112) formula (112) 224 General General CN General Formula (122) H H CH₃ H formula (112) formula (112) formula (112) 225 General General CN General Formula (122) H H CH₃O H formula (112) formula (112) formula (112) 226 General General CN General Formula (122) H H t-C₄H₉ H formula (112) formula (112) formula (112) 227 General General CN General Formula (122) H H Cl H formula (112) formula (112) formula (112) 228 General General CN General Formula (122) H H F H formula (112) formula (112) formula (112) 229 General General CN General Formula (122) H H H CH₃ formula (112) formula (112) formula (112) 230 General General CN General Formula (122) H H H CH₃O formula (112) formula (112) formula (112) 231 General General CN General Formula (123) H H H H formula (112) formula (112) formula (112) 232 General General CN General Formula (123) H CH₃ H H formula (112) formula (112) formula (112) 233 General General CN General Formula (123) H CH₃O H H formula (112) formula (112) formula (112) 234 General General CN General Formula (123) H H CH₃ H formula (112) formula (112) formula (112) 235 General General CN General Formula (123) H H CH₃O H formula (112) formula (112) formula (112) 236 General General CN General Formula (123) H H t-C₄H₉ H formula (112) formula (112) formula (112) 237 General General CN General Formula (123) H H Cl H formula (112) formula (112) formula (112) 238 General General CN General Formula (123) H H F H formula (112) formula (112) formula (112) 239 General General CN General Formula (123) H H H CH₃ formula (112) formula (112) formula (112) 240 General General CN General Formula (123) H H H CH₃O formula (112) formula (112) formula (112) 241 General General CN General Formula (124) H H H H formula (112) formula (112) formula (112) 242 General General CN General Formula (124) H CH₃ H H formula (112) formula (112) formula (112) 243 General General CN General Formula (124) H CH₃O H H formula (112) formula (112) formula (112) 244 General General CN General Formula (124) H H CH₃ H formula (112) formula (112) formula (112) 245 General General CN General Formula (124) H H CH₃O H formula (112) formula (112) formula (112) 246 General General CN General Formula (124) H H t-C₄H₉ H formula (112) formula (112) formula (112) 247 General General CN General Formula (124) H H Cl H formula (112) formula (112) formula (112) 248 General General CN General Formula (124) H H F H formula (112) formula (112) formula (112) 249 General General CN General Formula (124) H H H CH₃ formula (112) formula (112) formula (112) 250 General General CN General Formula (124) H H H CH₃O formula (112) formula (112) formula (112) 251 General General CN General General H C₆H₅ H H formula (112) formula (112) formula (112) formula (112) 252 General General CN General General H H C₅H₆ H formula (112) formula (112) formula (112) formula (112) 253 General General CN General H H C₆H₅ H H formula (112) formula (112) formula (112) 254 General General CN General H H H C₅H₆ H formula (112) formula (112) formula (112) 255 General General CN H H H C₆H₅ H H formula (112) formula (112) 256 General General CN H H H H C₆H₅ H formula (112) formula (112) 257 General H CN General H H C₆H₅ H H formula (112) formula (112) 258 General H CN General H H H C₆H₅ H formula (112) formula (112) 259 General H CN H General H C₆H₅ H H formula (112) formula (112) 260 General H CN H General H H C₆H₅ H formula (112) formula (112) 261 General H CN H H H C₆H₅ H H formula (112) 262 General H CN H H H H C₆H₅ H formula (112) 263 General General CN General F H C₆H₅ H H formula (112) formula (112) formula (112) 264 General General CN General F H H C₆H₅ H formula (112) formula (112) formula (112) 265 General General CN F F H C₆H₅ H H formula (112) formula (112) 266 General General CN F F H H C₆H₅ H formula (112) formula (112) 267 General F CN General F H C₆H₅ H H formula (112) formula (112) 268 General F CN General F H H C₆H₅ H formula (112) formula (112) 269 General F CN F General H C₆H₅ H H formula (112) formula (112) 270 General F CN F General H H C₆H₅ H formula (112) formula (112) 271 General F CN F F H C₆H₅ H H formula (112) 272 General F CN F F H H C₆H₅ H formula (112) 273 General General CN General OH H C₆H₅ H H formula (112) formula (112) formula (112) 274 General General CN General OH H H C₆H₅ H formula (112) formula (112) formula (112) 275 General General CN OH OH H C₆H₅ H H formula (112) formula (112) 276 General General CN OH OH H H C₆H₅ H formula (112) formula (112) 277 General OH CN General OH H C₆H₅ H H formula (112) formula (112) 278 General OH CN General OH H H C₆H₅ H formula (112) formula (112) 279 General OH CN OH General H C₆H₅ H H formula (112) formula (112) 280 General OH CN OH General H H C₆H₅ H formula (112) formula (112) 281 General OH CN OH OH H C₆H₅ H H formula (112) 282 General OH CN OH OH H H C₆H₅ H formula (112) 283 General General CN General Cl H C₆H₅ H H formula (112) formula (112) formula (112) 284 General General CN General Cl H H C₆H₅ H formula (112) formula (112) formula (112) 285 General General CN General F H C₆H₅ H H formula (112) formula (112) formula (112) 286 General General CN General F H H C₆H₅ H formula (112) formula (112) formula (112) 287 General General CN General CH₃O H C₆H₅ H H formula (112) formula (112) formula (112) 288 General General CN General CH₃O H H C₆H₅ H formula (112) formula (112) formula (112) 289 General General CN General C₂H₅O H C₆H₅ H H formula (112) formula (112) formula (112) 290 General General CN General C₂H₅O H H C₆H₅ H formula (112) formula (112) formula (112) 291 General General CN General C₆H₅O H C₆H₅ H H formula (112) formula (112) formula (112) 292 General General CN General C₆H₅O H H C₆H₅ H formula (112) formula (112) formula (112) 293 General General CN General Formula (121) H C₆H₅ H H formula (112) formula (112) formula (112) 294 General General CN General Formula (121) H H C₆H₅ H formula (112) formula (112) formula (112) 295 General General CN General Formula (122) H C₆H₅ H H formula (112) formula (112) formula (112) 296 General General CN General Formula (122) H H C₆H₅ H formula (112) formula (112) formula (112) 297 General General CN General Formula (123) H C₆H₅ H H formula (112) formula (112) formula (112) 298 General General CN General Formula (123) H H C₆H₅ H formula (112) formula (112) formula (112) 299 General General CN General Formula (124) H C₆H₅ H H formula (112) formula (112) formula (112) 300 General General CN General Formula (124) H H C₆H₅ H formula (112) formula (112) formula (112)

TABLE 2 Compound General formula (1) General formula (112) No. R¹ R² R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 301 General CN General General General H H H H formula (112) formula (112) formula (112) formula (112) 302 General CN General General General H CH₃ H H formula (112) formula (112) formula (112) formula (112) 303 General CN General General General H CH₃O H H formula (112) formula (112) formula (112) formula (112) 304 General CN General General General H H CH₃ H formula (112) formula (112) formula (112) formula (112) 305 General CN General General General H H CH₃O H formula (112) formula (112) formula (112) formula (112) 306 General CN General General General H H t-C₄H₉ H formula (112) formula (112) formula (112) formula (112) 307 General CN General General General H H Cl H formula (112) formula (112) formula (112) formula (112) 308 General CN General General General H H F H formula (112) formula (112) formula (112) formula (112) 309 General CN General General General H H H CH₃ formula (112) formula (112) formula (112) formula (112) 310 General CN General General General H H H CH₃O formula (112) formula (112) formula (112) formula (112) 311 General CN General General H H H H H formula (112) formula (112) formula (112) 312 General CN General General H H H CH₃ H formula (112) formula (112) formula (112) 313 General CN General General H H H CH₃O H formula (112) formula (112) formula (112) 314 General CN General H General H H H H formula (112) formula (112) formula (112) 315 General CN General H General H H CH₃ H formula (112) formula (112) formula (112) 316 General CN General H General H H CH₃O H formula (112) formula (112) formula (112) 317 General CN H General General H H H H formula (112) formula (112) formula (112) 318 General CN H General General H H CH₃ H formula (112) formula (112) formula (112) 319 General CN H General General H H CH₃O H formula (112) formula (112) formula (112) 320 H CN General General General H H H H formula (112) formula (112) formula (112) 321 H CN General General General H H CH₃ H formula (112) formula (112) formula (112) 322 H CN General General General H H CH₃O H formula (112) formula (112) formula (112) 323 General CN General H H H H H H formula (112) formula (112) 324 General CN General H H H H CH₃ H formula (112) formula (112) 325 General CN General H H H H CH₃O H formula (112) formula (112) 326 General CN H General H H H H H formula (112) formula (112) 327 General CN H General H H H CH₃ H formula (112) formula (112) 328 General CN H General H H H CH₃O H formula (112) formula (112) 329 H CN General General H H H H H formula (112) formula (112) 330 H CN General General H H H CH₃ H formula (112) formula (112) 331 H CN General General H H H CH₃O H formula (112) formula (112) 332 General CN H H General H H H H formula (112) formula (112) 333 General CN H H General H H CH₃ H formula (112) formula (112) 334 General CN H H General H H CH₃O H formula (112) formula (112) 335 H CN General H General H H H H formula (112) formula (112) 336 H CN General H General H H CH₃ H formula (112) formula (112) 337 H CN General H General H H CH₃O H formula (112) formula (112) 338 H CN H General General H H H H formula (112) formula (112) 339 H CN H General General H H CH₃ H formula (112) formula (112) 340 H CN H General General H H CH₃O H formula (112) formula (112) 341 General CN H H H H H H H formula (112) 342 General CN H H H H H CH₃ H formula (112) 343 General CN H H H H H CH₃O H formula (112) 344 H CN General H H H H H H formula (112) 345 H CN General H H H H CH₃ H formula (112) 346 H CN General H H H H CH₃O H formula (112) 347 H CN H General H H H H H formula (112) 348 H CN H General H H H CH₃ H formula (112) 349 H CN H General H H H CH₃O H formula (112) 350 General CN General General F H H H H formula (112) formula (112) formula (112) 351 General CN General General F H H CH₃ H formula (112) formula (112) formula (112) 352 General CN General General F H H CH₃O H formula (112) formula (112) formula (112) 353 General CN General F General H H H H formula (112) formula (112) formula (112) 354 General CN General F General H H CH₃ H formula (112) formula (112) formula (112) 355 General CN General F General H H CH₃O H formula (112) formula (112) formula (112) 356 General CN F General General H H H H formula (112) formula (112) formula (112) 357 General CN F General General H H CH₃ H formula (112) formula (112) formula (112) 358 General CN F General General H H CH₃O H formula (112) formula (112) formula (112) 359 F CN General General General H H H H formula (112) formula (112) formula (112) 360 F CN General General General H H CH₃ H formula (112) formula (112) formula (112) 361 F CN General General General H H CH₃O H formula (112) formula (112) formula (112) 362 General CN General F F H H H H formula (112) formula (112) 363 General CN General F F H H CH₃ H formula (112) formula (112) 364 General CN General F F H H CH₃O H formula (112) formula (112) 365 General CN F General F H H H H formula (112) formula (112) 366 General CN F General F H H CH₃ H formula (112) formula (112) 367 General CN F General F H H CH₃O H formula (112) formula (112) 368 F CN General General F H H H H formula (112) formula (112) 369 F CN General General F H H CH₃ H formula (112) formula (112) 370 F CN General General F H H CH₃O H formula (112) formula (112) 371 General CN F F General H H H H formula (112) formula (112) 372 General CN F F General H H CH₃ H formula (112) formula (112) 373 General CN F F General H H CH₃O H formula (112) formula (112) 374 F CN General F General H H H H formula (112) formula (112) 375 F CN General F General H H CH₃ H formula (112) formula (112) 376 F CN General F General H H CH₃O H formula (112) formula (112) 377 F CN F General General H H H H formula (112) formula (112) 378 F CN F General General H H CH₃ H formula (112) formula (112) 379 F CN F General General H H CH₃O H formula (112) formula (112) 380 General CN F F F H H H H formula (112) 381 General CN F F F H H CH₃ H formula (112) 382 General CN F F F H H CH₃O H formula (112) 383 F CN General F F H H H H formula (112) 384 F CN General F F H H CH₃ H formula (112) 385 F CN General F F H H CH₃O H formula (112) 386 F CN F General F H H H H formula (112) 387 F CN F General F H H CH₃ H formula (112) 388 F CN F General F H H CH₃O H formula (112) 389 General CN General General OH H H H H formula (112) formula (112) formula (112) 390 General CN General General OH H H CH₃ H formula (112) formula (112) formula (112) 391 General CN General General OH H H CH₃O H formula (112) formula (112) formula (112) 392 General CN General OH General H H H H formula (112) formula (112) formula (112) 393 General CN General OH General H H CH₃ H formula (112) formula (112) formula (112) 394 General CN General OH General H H CH₃O H formula (112) formula (112) formula (112) 395 General CN General OH General H H t-C₄H₉ H formula (112) formula (112) formula (112) 396 General CN General OH General H H Cl H formula (112) formula (112) formula (112) 397 General CN General OH General H H F H formula (112) formula (112) formula (112) 398 General CN OH General General H H H H formula (112) formula (112) formula (112) 399 General CN OH General General H H CH₃ H formula (112) formula (112) formula (112) 400 General CN OH General General H H CH₃O H formula (112) formula (112) formula (112) 401 OH CN General General General H H H H formula (112) formula (112) formula (112) 402 OH CN General General General H H CH₃ H formula (112) formula (112) formula (112) 403 OH CN General General General H H CH₃O H formula (112) formula (112) formula (112) 404 General CN General OH OH H H H H formula (112) formula (112) 405 General CN General OH OH H H CH₃ H formula (112) formula (112) 406 General CN General OH OH H H CH₃O H formula (112) formula (112) 407 General CN OH General OH H H H H formula (112) formula (112) 408 General CN OH General OH H H CH₃ H formula (112) formula (112) 409 General CN OH General OH H H CH₃O H formula (112) formula (112) 410 OH CN General General OH H H H H formula (112) formula (112) 411 OH CN General General OH H H CH₃ H formula (112) formula (112) 412 OH CN General General OH H H CH₃O H formula (112) formula (112) 413 General CN OH OH General H H H H formula (112) formula (112) 414 General CN OH OH General H H CH₃ H formula (112) formula (112) 415 General CN OH OH General H H CH₃O H formula (112) formula (112) 416 OH CN General OH General H H H H formula (112) formula (112) 417 OH CN General OH General H H CH₃ H formula (112) formula (112) 418 OH CN General OH General H H CH₃O H formula (112) formula (112) 419 OH CN OH General General H H H H formula (112) formula (112) 420 OH CN OH General General H H CH₃ H formula (112) formula (112) 421 OH CN OH General General H H CH₃O H formula (112) formula (112) 422 General CN OH OH OH H H H H formula (112) 423 General CN OH OH OH H H CH₃ H formula (112) 424 General CN OH OH OH H H CH₃O H formula (112) 425 OH CN General OH OH H H H H formula (112) 426 OH CN General OH OH H H CH₃ H formula (112) 427 OH CN General OH OH H H CH₃O H formula (112) 428 OH CN OH General OH H H H H formula (112) 429 OH CN OH General OH H H CH₃ H formula (112) 430 OH CN OH General OH H H CH₃O H formula (112) 431 OH CN OH OH General H H H H formula (112) 432 OH CN OH OH General H H CH₃ H formula (112) 433 OH CN OH OH General H H CH₃O H formula (112) 434 General CN General Cl General H H H H formula (112) formula (112) formula (112) 435 General CN General Cl General H H CH₃ H formula (112) formula (112) formula (112) 436 General CN General Cl General H H CH₃O H formula (112) formula (112) formula (112) 437 General CN General Cl General H H t-C₄H₉ H formula (112) formula (112) formula (112) 438 General CN General Cl General H H Cl H formula (112) formula (112) formula (112) 439 General CN General Cl General H H F H formula (112) formula (112) formula (112) 440 General CN General F General H H H H formula (112) formula (112) formula (112) 441 General CN General F General H H CH₃ H formula (112) formula (112) formula (112) 442 General CN General F General H H CH₃O H formula (112) formula (112) formula (112) 443 General CN General F General H H t-C₄H₉ H formula (112) formula (112) formula (112) 444 General CN General F General H H Cl H formula (112) formula (112) formula (112) 445 General CN General F General H H F H formula (112) formula (112) formula (112) 446 General CN General CH₃O General H H H H formula (112) formula (112) formula (112) 447 General CN General CH₃O General H H CH₃ H formula (112) formula (112) formula (112) 448 General CN General CH₃O General H H CH₃O H formula (112) formula (112) formula (112) 449 General CN General CH₃O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 450 General CN General CH₃O General H H Cl H formula (112) formula (112) formula (112) 451 General CN General CH₃O General H H F H formula (112) formula (112) formula (112) 452 General CN General C₂H₅O General H H H H formula (112) formula (112) formula (112) 453 General CN General C₂H₅O General H H CH₃ H formula (112) formula (112) formula (112) 454 General CN General C₂H₅O General H H CH₃O H formula (112) formula (112) formula (112) 455 General CN General C₂H₅O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 456 General CN General C₂H₅O General H H Cl H formula (112) formula (112) formula (112) 457 General CN General C₂H₅O General H H F H formula (112) formula (112) formula (112) 458 General CN General C₆H₅O General H H H H formula (112) formula (112) formula (112) 459 General CN General C₆H₅O General H H CH₃ H formula (112) formula (112) formula (112) 460 General CN General C₆H₅O General H H CH₃O H formula (112) formula (112) formula (112) 461 General CN General C₆H₅O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 462 General CN General C₆H₅O General H H Cl H formula (112) formula (112) formula (112) 463 General CN General C₆H₅O General H H F H formula (112) formula (112) formula (112) 464 General CN General Formula (121) General H H H H formula (112) formula (112) formula (112) 465 General CN General Formula (121) General H H CH₃ H formula (112) formula (112) formula (112) 466 General CN General Formula (121) General H H CH₃O H formula (112) formula (112) formula (112) 467 General CN General Formula (121) General H H t-C₄H₉ H formula (112) formula (112) formula (112) 468 General CN General Formula (121) General H H Cl H formula (112) formula (112) formula (112) 469 General CN General Formula (121) General H H F H formula (112) formula (112) formula (112) 470 General CN General Formula (122) General H H H H formula (112) formula (112) formula (112) 471 General CN General Formula (122) General H H CH₃ H formula (112) formula (112) formula (112) 472 General CN General Formula (122) General H H CH₃O H formula (112) formula (112) formula (112) 473 General CN General Formula (122) General H H t-C₄H₉ H formula (112) formula (112) formula (112) 474 General CN General Formula (122) General H H Cl H formula (112) formula (112) formula (112) 475 General CN General Formula (122) General H H F H formula (112) formula (112) formula (112) 476 General CN General Formula (123) General H H H H formula (112) formula (112) formula (112) 477 General CN General Formula (123) General H H CH₃ H formula (112) formula (112) formula (112) 478 General CN General Formula (123) General H H CH₃O H formula (112) formula (112) formula (112) 479 General CN General Formula (123) General H H t-C₄H₉ H formula (112) formula (112) formula (112) 480 General CN General Formula (123) General H H Cl H formula (112) formula (112) formula (112) 481 General CN General Formula (123) General H H F H formula (112) formula (112) formula (112) 482 General CN General Formula (124) General H H H H formula (112) formula (112) formula (112) 483 General CN General Formula (124) General H H CH₃ H formula (112) formula (112) formula (112) 484 General CN General Formula (124) General H H CH₃O H formula (112) formula (112) formula (112) 485 General CN General Formula (124) General H H t-C₄H₉ H formula (112) formula (112) formula (112) 486 General CN General Formula (124) General H H Cl H formula (112) formula (112) formula (112) 487 General CN General Formula (124) General H H F H formula (112) formula (112) formula (112) 488 General CN General General General H C₆H₅ H H formula (112) formula (112) formula (112) formula (112) 489 General CN General General General H H C₆H₅ H formula (112) formula (112) formula (112) formula (112) 490 General CN General General H H C₆H₅ H H formula (112) formula (112) formula (112) 491 General CN General General H H H C₆H₅ H formula (112) formula (112) formula (112) 492 General CN General H General H C₆H₅ H H formula (112) formula (112) formula (112) 493 General CN General H General H H C₆H₅ H formula (112) formula (112) formula (112) 494 General CN H General General H C₆H₅ H H formula (112) formula (112) formula (112) 495 General CN H General General H H C₆H₅ H formula (112) formula (112) formula (112) 496 H CN General General General H C₆H₅ H H formula (112) formula (112) formula (112) 497 H CN General General General H H C₆H₅ H formula (112) formula (112) formula (112) 498 General CN General H H H C₆H₅ H H formula (112) formula (112) 499 General CN General H H H H C₆H₅ H formula (112) formula (112)   500-1 General CN H General H H C₆H₅ H H formula (112) formula (112)   500-2 General CN H General H H H C₆H₅ H formula (112) formula (112)   500-3 H CN General General H H C₆H₅ H H formula (112) formula (112)   500-4 H CN General General H H H C₆H₅ H formula (112) formula (112)   500-5 General CN H H General H C₆H₅ H H formula (112) formula (112)   500-6 General CN H H General H H C₆H₅ H formula (112) formula (112)   500-7 H CN General H General H C₆H₅ H H formula (112) formula (112)   500-8 H CN General H General H H C₆H₅ H formula (112) formula (112)   500-9 H CN H General General H C₆H₅ H H formula (112) formula (112)   500-10 H CN H General General H H C₆H₅ H formula (112) formula (112)   500-11 General CN H H H H C₆H₅ H H formula (112)   500-12 General CN H H H H H C₆H₅ H formula (112)   500-13 H CN General H H H C₆H₅ H H formula (112)   500-14 H CN General H H H H C₆H₅ H formula (112)   500-15 H CN H General H H C₆H₅ H H formula (112)   500-16 H CN H General H H H C₆H₅ H formula (112)   500-17 General CN General General F H H C₆H₅ H formula (112) formula (112) formula (112)   500-18 General CN General F General H H C₆H₅ H formula (112) formula (112) formula (112)   500-19 General CN F General General H H C₆H₅ H formula (112) formula (112) formula (112)   500-20 F CN General General General H H C₆H₅ H formula (112) formula (112) formula (112)   500-21 General CN General F F H H C₆H₅ H formula (112) formula (112)   500-22 General CN F General F H H C₆H₅ H formula (112) formula (112)   500-23 F CN General General F H H C₆H₅ H formula (112) formula (112)   500-24 General CN F F General H H C₆H₅ H formula (112) formula (112)   500-25 F CN General F General H H C₆H₅ H formula (112) formula (112)   500-26 F CN F General General H H C₆H₅ H formula (112) formula (112)   500-27 General CN F F F H H C₆H₅ H formula (112)   500-28 F CN General F F H H C₆H₅ H formula (112)   500-29 F CN F General F H H C₆H₅ H formula (112)   500-30 General CN General General OH H H C₆H₅ H formula (112) formula (112) formula (112)   500-31 General CN General OH General H H C₆H₅ H formula (112) formula (112) formula (112)   500-32 General CN OH General General H H C₆H₅ H formula (112) formula (112) formula (112)   500-33 OH CN General General General H H C₆H₅ H formula (112) formula (112) formula (112)   500-34 General CN General OH OH H H C₆H₅ H formula (112) formula (112)   500-35 General CN OH General OH H H C₆H₅ H formula (112) formula (112)   500-36 OH CN General General OH H H C₆H₅ H formula (112) formula (112)   500-37 General CN OH OH General H H C₆H₅ H formula (112) formula (112)   500-38 OH CN General OH General H H C₆H₅ H formula (112) formula (112)   500-39 OH CN OH General General H H C₆H₅ H formula (112) formula (112)   500-40 General CN OH OH OH H H C₆H₅ H formula (112)   500-41 OH CN General OH OH H H C₆H₅ H formula (112)   500-42 OH CN OH General OH H H C₆H₅ H formula (112)   500-43 OH CN OH OH General H H C₆H₅ H formula (112)   500-44 General CN General Cl General H H C₆H₅ H formula (112) formula (112) formula (112)   500-45 General CN General F General H H C₆H₅ H formula (112) formula (112) formula (112)   500-46 General CN General CH₃O General H H C₆H₅ H formula (112) formula (112) formula (112)   500-47 General CN General C₂H₅O General H H C₆H₅ H formula (112) formula (112) formula (112)   500-48 General CN General C₆H₅O General H H C₆H₅ H formula (112) formula (112) formula (112)   500-49 General CN General Formula (121) General H H C₆H₅ H formula (112) formula (112) formula (112)   500-50 General CN General Formula (122) General H H C₆H₅ H formula (112) formula (112) formula (112)   500-51 General CN General Formula (123) General H H C₆H₅ H formula (112) formula (112) formula (112)   500-52 General CN General Formula (124) General H H C₆H₅ H formula (112) formula (112) formula (112)

TABLE 3 Compound General formula (1) General formula (112) No. R¹ R² R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 501 CN General formula (112) General formula (112) General formula (112) General formula (112) H H H H 502 CN General formula (112) General formula (112) General formula (112) General formula (112) H CH₃ H H 503 CN General formula (112) General formula (112) General formula (112) General formula (112) H CH₃O H H 504 CN General formula (112) General formula (112) General formula (112) General formula (112) H H CH₃ H 505 CN General formula (112) General formula (112) General formula (112) General formula (112) H H CH₃O H 506 CN General formula (112) General formula (112) General formula (112) General formula (112) H H t-C₄H₉ H 507 CN General formula (112) General formula (112) General formula (112) General formula (112) H H Cl H 508 CN General formula (112) General formula (112) General formula (112) General formula (112) H H F H 509 CN General formula (112) General formula (112) General formula (112) General formula (112) H H H CH₃ 510 CN General formula (112) General formula (112) General formula (112) General formula (112) H H H CH₃O 511 CN General formula (112) General formula (112) General formula (112) H H H H H 512 CN General formula (112) General formula (112) General formula (112) H H H CH₃ H 513 CN General formula (112) General formula (112) General formula (112) H H H CH₃O H 514 CN General formula (112) General formula (112) H General formula (112) H H H H 515 CN General formula (112) General formula (112) H General formula (112) H H CH₃ H 516 CN General formula (112) General formula (112) H General formula (112) H H CH₃O H 517 CN General formula (112) General formula (112) H H H H H H 518 CN General formula (112) General formula (112) H H H H CH₃ H 519 CN General formula (112) General formula (112) H H H H CH₃O H 520 CN General formula (112) H General formula (112) H H H H H 521 CN General formula (112) H General formula (112) H H H CH₃ H 522 CN General formula (112) H General formula (112) H H H CH₃O H 523 CN H General formula (112) General formula (112) H H H H H 524 CN H General formula (112) General formula (112) H H H CH₃ H 525 CN H General formula (112) General formula (112) H H H CH₃O H 526 CN General formula (112) H H General formula (112) H H H H 527 CN General formula (112) H H General formula (112) H H CH₃ H 528 CN General formula (112) H H General formula (112) H H CH₃O H 529 CN General formula (112) H H H H H H H 530 CN General formula (112) H H H H H CH₃ H 531 CN General formula (112) H H H H H CH₃O H 532 CN H General formula (112) H H H H H H 533 CN H General formula (112) H H H H CH₃ H 534 CN H General formula (112) H H H H CH₃O H 535 CN General formula (112) General formula (112) General formula (112) F H H H H 536 CN General formula (112) General formula (112) General formula (112) F H H CH₃ H 537 CN General formula (112) General formula (112) General formula (112) F H H CH₃O H 538 CN General formula (112) General formula (112) F General formula (112) H H H H 539 CN General formula (112) General formula (112) F General formula (112) H H CH₃ H 540 CN General formula (112) General formula (112) F General formula (112) H H CH₃O H 541 CN General formula (112) General formula (112) F F H H H H 542 CN General formula (112) General formula (112) F F H H CH₃ H 543 CN General formula (112) General formula (112) F F H H CH₃O H 544 CN General formula (112) F General formula (112) F H H H H 545 CN General formula (112) F General formula (112) F H H CH₃ H 546 CN General formula (112) F General formula (112) F H H CH₃O H 547 CN F General formula (112) General formula (112) F H H H H 548 CN F General formula (112) General formula (112) F H H CH₃ H 549 CN F General formula (112) General formula (112) F H H CH₃O H 550 CN General formula (112) F F General formula (112) H H H H 551 CN General formula (112) F F General formula (112) H H CH₃ H 552 CN General formula (112) F F General formula (112) H H CH₃O H 553 CN General formula (112) F F F H H H H 554 CN General formula (112) F F F H H CH₃ H 555 CN General formula (112) F F F H H CH₃O H 556 CN F General formula (112) F F H H H H 557 CN F General formula (112) F F H H CH₃ H 558 CN F General formula (112) F F H H CH₃O H 559 CN General formula (112) General formula (112) General formula (112) OH H H H H 560 CN General formula (112) General formula (112) General formula (112) OH H H CH₃ H 561 CN General formula (112) General formula (112) General formula (112) OH H H CH₃O H 562 CN General formula (112) General formula (112) OH General formula (112) H H H H 563 CN General formula (112) General formula (112) OH General formula (112) H H CH₃ H 564 CN General formula (112) General formula (112) OH General formula (112) H H CH₃O H 565 CN General formula (112) General formula (112) OH General formula (112) H H Cl H 566 CN General formula (112) General formula (112) OH General formula (112) H H F H 567 CN General formula (112) General formula (112) OH OH H H H H 568 CN General formula (112) General formula (112) OH OH H H CH₃ H 569 CN General formula (112) General formula (112) OH OH H H CH₃O H 570 CN General formula (112) OH General formula (112) OH H H H H 571 CN General formula (112) OH General formula (112) OH H H CH₃ H 572 CN General formula (112) OH General formula (112) OH H H CH₃O H 573 CN OH General formula (112) General formula (112) OH H H H H 574 CN OH General formula (112) General formula (112) OH H H CH₃ H 575 CN OH General formula (112) General formula (112) OH H H CH₃O H 576 CN General formula (112) OH OH General formula (112) H H H H 577 CN General formula (112) OH OH General formula (112) H H CH₃ H 578 CN General formula (112) OH OH General formula (112) H H CH₃O H 579 CN General formula (112) OH OH OH H H H H 580 CN General formula (112) OH OH OH H H CH₃ H 581 CN General formula (112) OH OH OH H H CH₃O H 582 CN OH General formula (112) OH OH H H H H 583 CN OH General formula (112) OH OH H H CH₃ H 584 CN OH General formula (112) OH OH H H CH₃O H 585 CN General formula (112) General formula (112) Cl General formula (112) H H H H 586 CN General formula (112) General formula (112) Cl General formula (112) H H CH₃ H 587 CN General formula (112) General formula (112) Cl General formula (112) H H CH₃O H 588 CN General formula (112) General formula (112) Cl General formula (112) H H t-C₄H₉ H 589 CN General formula (112) General formula (112) Cl General formula (112) H H Cl H 590 CN General formula (112) General formula (112) Cl General formula (112) H H F H 591 CN General formula (112) General formula (112) F General formula (112) H H H H 592 CN General formula (112) General formula (112) F General formula (112) H H CH₃ H 593 CN General formula (112) General formula (112) F General formula (112) H H CH₃O H 594 CN General formula (112) General formula (112) F General formula (112) H H t-C₄H₉ H 595 CN General formula (112) General formula (112) F General formula (112) H H Cl H 596 CN General formula (112) General formula (112) F General formula (112) H H F H 597 CN General formula (112) General formula (112) CH₃O General formula (112) H H H H 598 CN General formula (112) General formula (112) CH₃O General formula (112) H H CH₃ H 599 CN General formula (112) General formula (112) CH₃O General formula (112) H H CH₃O H 600 CN General formula (112) General formula (112) CH₃O General formula (112) H H t-C₄H₉ H 601 CN General formula (112) General formula (112) CH₃O General formula (112) H H Cl H 602 CN General formula (112) General formula (112) CH₃O General formula (112) H H F H 603 CN General formula (112) General formula (112) C₂H₅O General formula (112) H H H H 604 CN General formula (112) General formula (112) C₂H₅O General formula (112) H H CH₃ H 605 CN General formula (112) General formula (112) C₂H₅O General formula (112) H H CH₃O H 606 CN General formula (112) General formula (112) C₃H₅O General formula (112) H H t-C₄H₉ H 607 CN General formula (112) General formula (112) C₂H₅O General formula (112) H H Cl H 608 CN General formula (112) General formula (112) C₂H₅O General formula (112) H H F H 609 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H H H 610 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H CH₃ H 611 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H CH₃O H 612 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H t-C₄H₉ H 613 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H Cl H 614 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H F H 615 CN General formula (112) General formula (112) Formula (121) General formula (112) H H H H 616 CN General formula (112) General formula (112) Formula (121) General formula (112) H H CH₃ H 617 CN General formula (112) General formula (112) Formula (121) General formula (112) H H CH₃O H 618 CN General formula (112) General formula (112) Formula (121) General formula (112) H H t-C₄H₉ H 619 CN General formula (112) General formula (112) Formula (121) General formula (112) H H Cl H 620 CN General formula (112) General formula (112) Formula (121) General formula (112) H H F H 621 CN General formula (112) General formula (112) Formula (122) General formula (112) H H H H 622 CN General formula (112) General formula (112) Formula (122) General formula (112) H H CH₃ H 623 CN General formula (112) General formula (112) Formula (122) General formula (112) H H CH₃O H 624 CN General formula (112) General formula (112) Formula (122) General formula (112) H H t-C₄H₉ H 625 CN General formula (112) General formula (112) Formula (122) General formula (112) H H Cl H 626 CN General formula (112) General formula (112) Formula (122) General formula (112) H H F H 627 CN General formula (112) General formula (112) Formula (123) General formula (112) H H H H 628 CN General formula (112) General formula (112) Formula (123) General formula (112) H H CH₃ H 629 CN General formula (112) General formula (112) Formula (123) General formula (112) H H CH₃O H 630 CN General formula (112) General formula (112) Formula (123) General formula (112) H H t-C₄H₉ H 631 CN General formula (112) General formula (112) Formula (123) General formula (112) H H Cl H 632 CN General formula (112) General formula (112) Formula (123) General formula (112) H H F H 633 CN General formula (112) General formula (112) Formula (124) General formula (112) H H H H 634 CN General formula (112) General formula (112) Formula (124) General formula (112) H H CH₃ H 635 CN General formula (112) General formula (112) Formula (124) General formula (112) H H CH₃O H 636 CN General formula (112) General formula (112) Formula (124) General formula (112) H H t-C₄H₉ H 637 CN General formula (112) General formula (112) Formula (124) General formula (112) H H Cl H 638 CN General formula (112) General formula (112) Formula (124) General formula (112) H H F H 639 CN General formula (112) General formula (112) General formula (112) General formula (112) H C₆H₅ H H 640 CN General formula (112) General formula (112) General formula (112) General formula (112) H H C₆H₅ H 641 CN General formula (112) General formula (112) General formula (112) H H C₆H₅ H H 642 CN General formula (112) General formula (112) General formula (112) H H H C₆H₅ H 643 CN General formula (112) General formula (112) H General formula (112) H C₆H₅ H H 644 CN General formula (112) General formula (112) H General formula (112) H H C₆H₅ H 645 CN General formula (112) General formula (112) H H H C₆H₅ H H 646 CN General formula (112) General formula (112) H H H H C₆H₅ H 647 CN General formula (112) H General formula (112) H H C₆H₅ H H 648 CN General formula (112) H General formula (112) H H H C₆H₅ H 649 CN H General formula (112) General formula (112) H H C₆H₅ H H 650 CN H General formula (112) General formula (112) H H H C₆H₅ H 651 CN H H General formula (112) General formula (112) H C₆H₅ H H 652 CN H H General formula (112) General formula (112) H H C₆H₅ H 653 CN General formula (112) H H H H C₆H₅ H H 654 CN General formula (112) H H H H H C₆H₅ H 655 CN H General formula (112) H H H C₆H₅ H H 656 CN H General formula (112) H H H H C₆H₅ H 657 CN General formula (112) General formula (112) General formula (112) F H H C₆H₅ H 658 CN General formula (112) General formula (112) F General formula (112) H H C₆H₅ H 659 CN General formula (112) General formula (112) F F H H C₆H₅ H 660 CN General formula (112) F General formula (112) F H H C₆H₅ H 661 CN F General formula (112) General formula (112) F H H C₆H₅ H 662 CN F F General formula (112) General formula (112) H H C₆H₅ H 663 CN General formula (112) F F F H H C₆H₅ H 664 CN F General formula (112) F F H H C₆H₅ H 665 CN General formula (112) General formula (112) General formula (112) OH H H C₆H₅ H 666 CN General formula (112) General formula (112) OH General formula (112) H H C₆H₅ H 667 CN General formula (112) General formula (112) OH OH H H C₆H₅ H 668 CN General formula (112) OH General formula (112) OH H H C₆H₅ H 669 CN OH General formula (112) General formula (112) OH H H C₆H₅ H 670 CN OH OH General formula (112) General formula (112) H H C₆H₅ H 671 CN General formula (112) OH OH OH H H C₆H₅ H 672 CN OH General formula (112) OH OH H H C₆H₅ H 673 CN General formula (112) General formula (112) Cl General formula (112) H H C₆H₅ H 674 CN General formula (112) General formula (112) F General formula (112) H H C₆H₅ H 675 CN General formula (112) General formula (112) CH₃O General formula (112) H H C₆H₅ H 676 CN General formula (112) General formula (112) C₂H₅O General formula (112) H H C₆H₅ H 677 CN General formula (112) General formula (112) C₆H₅O General formula (112) H H C₆H₅ H 678 CN General formula (112) General formula (112) Formula (121) General formula (112) H H C₆H₅ H 679 CN General formula (112) General formula (112) Formula (122) General formula (112) H H C₆H₅ H 680 CN General formula (112) General formula (112) Formula (123) General formula (112) H H C₆H₅ H 681 CN General formula (112) General formula (112) Formula (124) General formula (112) H H C₆H₅ H

TABLE 4 General formula (1) General formula (113) Compound No. R¹ R² R³ R⁴ R⁵ R⁴¹ R⁴² R⁴³ R⁴⁴ R⁴⁵ R⁴⁶ 701 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H H 702 General formula (113) General formula (113) CN General formula (113) General formula (113) H CH₃ H H H H 703 General formula (113) General formula (113) CN General formula (113) General formula (113) H CH₃O H H H H 704 General formula (113) General formula (113) CN General formula (113) General formula (113) H H CH₃ H H H 705 General formula (113) General formula (113) CN General formula (113) General formula (113) H H CH₃O H H H 706 General formula (113) General formula (113) CN General formula (113) General formula (113) H H t-C₄H₉ H H H 707 General formula (113) General formula (113) CN General formula (113) General formula (113) H H Cl H H H 708 General formula (113) General formula (113) CN General formula (113) General formula (113) H H F H H H 709 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H CH₃ H H 710 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H CH₃O H H 711 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H CH₃ H 712 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H CH₃O H 713 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H t-C₄H₉ H 714 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H Cl H 715 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H F H 716 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H C₆H₅ H 717 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H p-CH₃C₆H₄ H 718 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H 2,4,6-(CH₃)₃C₆H₂ H 719 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H p-CH₃OC₆H₄ H 720 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H p-(CH₃)₂NC₆H₄ H 721 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H p-FC₆H₄ H 722 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H p-CNC₆H₄ H 723 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H CH₃ 724 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H CH₃O 725 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H t-C₄H₉ 726 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H Cl 727 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H F 728 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H C₆H₅ 729 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H p-CH₃C₆H₄ 730 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H 2,4,6-(CH₃)₃C₆H₂ 731 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H p-CH₃OC₆H₄ 732 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H p-(CH₃)₂NC₆H₄ 733 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H p-FC₆H₄ 734 General formula (113) General formula (113) CN General formula (113) General formula (113) H H H H H p-CNC₆H₄ 735 General formula (113) General formula (113) CN General formula (113) H H H H H H H 736 General formula (113) General formula (113) CN H General formula (113) H H H H H H 737 General formula (113) General formula (113) CN H H H H H H H H 738 General formula (113) H CN General formula (113) H H H H H H H 739 H General formula (113) CN General formula (113) H H H H H H H 740 General formula (113) H CN H H H H H H H H 741 General formula (113) General formula (113) CN General formula (113) F H H H H H H 742 General formula (113) General formula (113) CN F General formula (113) H H H H H H 743 General formula (113) General formula (113) CN F F H H H H H H 744 General formula (113) F CN General formula (113) F H H H H H H 745 F General formula (113) CN General formula (113) F H H H H H H 746 General formula (113) F CN F F H H H H H H 747 General formula (113) General formula (113) CN General formula (113) OH H H H H H H 748 General formula (113) General formula (113) CN OH General formula (113) H H H H H H 749 General formula (113) General formula (113) CN OH OH H H H H H H 750 General formula (113) OH CN General formula (113) OH H H H H H H 751 OH General formula (113) CN General formula (113) OH H H H H H H 752 General formula (113) OH CN OH OH H H H H H H 753 General formula (113) General formula (113) CN Cl General formula (113) H H H H H H 754 General formula (113) General formula (113) CN Cl General formula (113) H H CH₃ H H H 755 General formula (113) General formula (113) CN Cl General formula (113) H H CH₃O H H H 756 General formula (113) General formula (113) CN Cl General formula (113) H H t-C₄H₉ H H H 757 General formula (113) General formula (113) CN Cl General formula (113) H H Cl H H H 758 General formula (113) General formula (113) CN Cl General formula (113) H H F H H H 759 General formula (113) General formula (113) CN F General formula (113) H H H H H H 760 General formula (113) General formula (113) CN F General formula (113) H H CH₃ H H H 761 General formula (113) General formula (113) CN F General formula (113) H H CH₃O H H H 762 General formula (113) General formula (113) CN F General formula (113) H H t-C₄H₉ H H H 763 General formula (113) General formula (113) CN F General formula (113) H H Cl H H H 764 General formula (113) General formula (113) CN F General formula (113) H H F H H H 765 General formula (113) General formula (113) CN CH₃O General formula (113) H H H H H H 766 General formula (113) General formula (113) CN CH₃O General formula (113) H H CH₃ H H H 767 General formula (113) General formula (113) CN CH₃O General formula (113) H H CH₃O H H H 768 General formula (113) General formula (113) CN CH₃O General formula (113) H H t-C₄H₉ H H H 769 General formula (113) General formula (113) CN CH₃O General formula (113) H H Cl H H H 770 General formula (113) General formula (113) CN CH₃O General formula (113) H H F H H H 771 General formula (113) General formula (113) CN C₂H₅O General formula (113) H H H H H H 772 General formula (113) General formula (113) CN C₂H₅O General formula (113) H H CH₃ H H H 773 General formula (113) General formula (113) CN C₂H₅O General formula (113) H H CH₃O H H H 774 General formula (113) General formula (113) CN C₂H₅O General formula (113) H H t-C₄H₉ H H H 775 General formula (113) General formula (113) CN C₂H₅O General formula (113) H H Cl H H H 776 General formula (113) General formula (113) CN C₂H₅O General formula (113) H H F H H H 777 General formula (113) General formula (113) CN C₆H₅O General formula (113) H H H H H H 778 General formula (113) General formula (113) CN C₆H₅O General formula (113) H H CH₃ H H H 779 General formula (113) General formula (113) CN C₆H₅O General formula (113) H H CH₃O H H H 780 General formula (113) General formula (113) CN C₆H₅O General formula (113) H H t-C₄H₉ H H H 781 General formula (113) General formula (113) CN C₆H₅O General formula (113) H H Cl H H H 782 General formula (113) General formula (113) CN C₆H₅O General formula (113) H H F H H H 783 General formula (113) General formula (113) CN Formula (121) General formula (113) H H H H H H 784 General formula (113) General formula (113) CN Formula (121) General formula (113) H H CH₃ H H H 785 General formula (113) General formula (113) CN Formula (121) General formula (113) H H CH₃O H H H 786 General formula (113) General formula (113) CN Formula (121) General formula (113) H H t-C₄H₉ H H H 787 General formula (113) General formula (113) CN Formula (121) General formula (113) H H Cl H H H 788 General formula (113) General formula (113) CN Formula (121) General formula (113) H H F H H H 789 General formula (113) General formula (113) CN Formula (122) General formula (113) H H H H H H 790 General formula (113) General formula (113) CN Formula (122) General formula (113) H H CH₃ H H H 791 General formula (113) General formula (113) CN Formula (122) General formula (113) H H CH₃O H H H 792 General formula (113) General formula (113) CN Formula (122) General formula (113) H H t-C₄H₉ H H H 793 General formula (113) General formula (113) CN Formula (122) General formula (113) H H Cl H H H 794 General formula (113) General formula (113) CN Formula (122) General formula (113) H H F H H H 795 General formula (113) General formula (113) CN Formula (123) General formula (113) H H H H H H 796 General formula (113) General formula (113) CN Formula (123) General formula (113) H H CH₃ H H H 797 General formula (113) General formula (113) CN Formula (123) General formula (113) H H CH₃O H H H 798 General formula (113) General formula (113) CN Formula (123) General formula (113) H H t-C₄H₉ H H H 799 General formula (113) General formula (113) CN Formula (123) General formula (113) H H Cl H H H 800 General formula (113) General formula (113) CN Formula (123) General formula (113) H H F H H H 801 General formula (113) General formula (113) CN Formula (124) General formula (113) H H H H H H 802 General formula (113) General formula (113) CN Formula (124) General formula (113) H H CH₃ H H H 803 General formula (113) General formula (113) CN Formula (124) General formula (113) H H CH₃O H H H 804 General formula (113) General formula (113) CN Formula (124) General formula (113) H H t-C₄H₉ H H H 805 General formula (113) General formula (113) CN Formula (124) General formula (113) H H Cl H H H 806 General formula (113) General formula (113) CN Formula (124) General formula (113) H H F H H H

TABLE 5 General formula (114) R⁵¹, Compound General formula (1) R⁵⁶, R⁵⁸, No. R¹ R² R³ R⁴ R⁵ R⁵² R⁵³ R⁵⁴ R⁵⁵ R⁵⁷ R⁵⁹ R⁶¹ R⁶⁰, R⁶² 901 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H H H H H 902 General formula (114) General formula (114) CN General formula (114) General formula (114) CH₃ H H H H H H H 903 General formula (114) General formula (114) CN General formula (114) General formula (114) CH₃O H H H H H H H 904 General formula (114) General formula (114) CN General formula (114) General formula (114) H CH₃ H H H H H H 905 General formula (114) General formula (114) CN General formula (114) General formula (114) H CH₃O H H H H H H 906 General formula (114) General formula (114) CN General formula (114) General formula (114) H t-C₄H₉ H H H H H H 907 General formula (114) General formula (114) CN General formula (114) General formula (114) H Cl H H H H H H 908 General formula (114) General formula (114) CN General formula (114) General formula (114) H F H H H H H H 909 General formula (114) General formula (114) CN General formula (114) General formula (114) H H CH₃ H H H H H 910 General formula (114) General formula (114) CN General formula (114) General formula (114) H H CH₃O H H H H H 911 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H CH₃ H H H H 912 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H CH₃O H H H H 913 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H CH₃ H H H 914 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H CH₃O H H H 915 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H H CH₃ H H 916 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H H CH₃O H H 917 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H H H CH₃ H 918 General formula (114) General formula (114) CN General formula (114) General formula (114) H H H H H H CH₃O H 919 General formula (114) General formula (114) CN General formula (114) H H H H H H H H H 920 General formula (114) General formula (114) CN H General formula (114) H H H H H H H H 921 General formula (114) General formula (114) CN H H H H H H H H H H 922 General formula (114) H CN General formula (114) H H H H H H H H H 923 H General formula (114) CN General formula (114) H H H H H H H H H 924 General formula (114) H CN H H H H H H H H H H 925 General formula (114) General formula (114) CN General formula (114) F H H H H H H H H 926 General formula (114) General formula (114) CN F General formula (114) H H H H H H H H 927 General formula (114) General formula (114) CN F F H H H H H H H H 928 General formula (114) F CN General formula (114) F H H H H H H H H 929 F General formula (114) CN General formula (114) F H H H H H H H H 930 General formula (114) F CN F F H H H H H H H H 931 General formula (114) General formula (114) CN General formula (114) OH H H H H H H H H 932 General formula (114) General formula (114) CN OH General formula (114) H H H H H H H H 933 General formula (114) General formula (114) CN OH OH H H H H H H H H 934 General formula (114) OH CN General formula (114) OH H H H H H H H H 935 OH General formula (114) CN General formula (114) OH H H H H H H H H 936 General formula (114) OH CN OH OH H H H H H H H H 937 General formula (114) General formula (114) CN Cl General formula (114) H H H H H H H H 938 General formula (114) General formula (114) CN Cl General formula (114) H CH₃ H H H H H H 939 General formula (114) General formula (114) CN Cl General formula (114) H CH₃O H H H H H H 940 General formula (114) General formula (114) CN Cl General formula (114) H t-C₄H₉ H H H H H H 941 General formula (114) General formula (114) CN Cl General formula (114) H Cl H H H H H H 942 General formula (114) General formula (114) CN Cl General formula (114) H F H H H H H H 943 General formula (114) General formula (114) CN F General formula (114) H H H H H H H H 944 General formula (114) General formula (114) CN F General formula (114) H CH₃ H H H H H H 945 General formula (114) General formula (114) CN F General formula (114) H CH₃O H H H H H H 946 General formula (114) General formula (114) CN F General formula (114) H t-C₄H₉ H H H H H H 947 General formula (114) General formula (114) CN F General formula (114) H Cl H H H H H H 948 General formula (114) General formula (114) CN F General formula (114) H F H H H H H H 949 General formula (114) General formula (114) CN CH₃O General formula (114) H H H H H H H H 950 General formula (114) General formula (114) CN CH₃O General formula (114) H CH₃ H H H H H H 951 General formula (114) General formula (114) CN CH₃O General formula (114) H CH₃O H H H H H H 952 General formula (114) General formula (114) CN CH₃O General formula (114) H t-C₄H₉ H H H H H H 953 General formula (114) General formula (114) CN CH₃O General formula (114) H Cl H H H H H H 954 General formula (114) General formula (114) CN CH₃O General formula (114) H F H H H H H H 955 General formula (114) General formula (114) CN C₂H₅O General formula (114) H H H H H H H H 956 General formula (114) General formula (114) CN C₂H₅O General formula (114) H CH₃ H H H H H H 957 General formula (114) General formula (114) CN C₂H₅O General formula (114) H CH₃O H H H H H H 958 General formula (114) General formula (114) CN C₂H₅O General formula (114) H t-C₄H₉ H H H H H H 959 General formula (114) General formula (114) CN C₂H₅O General formula (114) H Cl H H H H H H 960 General formula (114) General formula (114) CN C₂H₅O General formula (114) H F H H H H H H 961 General formula (114) General formula (114) CN C₆H₅O General formula (114) H H H H H H H H 962 General formula (114) General formula (114) CN C₆H₅O General formula (114) H CH₃ H H H H H H 963 General formula (114) General formula (114) CN C₆H₅O General formula (114) H CH₃O H H H H H H 964 General formula (114) General formula (114) CN C₆H₅O General formula (114) H t-C₄H₉ H H H H H H 965 General formula (114) General formula (114) CN C₆H₅O General formula (114) H Cl H H H H H H 966 General formula (114) General formula (114) CN C₆H₅O General formula (114) H F H H H H H H 967 General formula (114) General formula (114) CN Formula (121) General formula (114) H H H H H H H H 968 General formula (114) General formula (114) CN Formula (121) General formula (114) H CH₃ H H H H H H 969 General formula (114) General formula (114) CN Formula (121) General formula (114) H CH₃O H H H H H H 970 General formula (114) General formula (114) CN Formula (121) General formula (114) H t-C₄H₉ H H H H H H 971 General formula (114) General formula (114) CN Formula (121) General formula (114) H Cl H H H H H H 972 General formula (114) General formula (114) CN Formula (121) General formula (114) H F H H H H H H 973 General formula (114) General formula (114) CN Formula (122) General formula (114) H H H H H H H H 974 General formula (114) General formula (114) CN Formula (122) General formula (114) H CH₃ H H H H H H 975 General formula (114) General formula (114) CN Formula (122) General formula (114) H CH₃O H H H H H H 976 General formula (114) General formula (114) CN Formula (122) General formula (114) H t-C₄H₉ H H H H H H 977 General formula (114) General formula (114) CN Formula (122) General formula (114) H Cl H H H H H H 978 General formula (114) General formula (114) CN Formula (122) General formula (114) H F H H H H H H 989 General formula (114) General formula (114) CN Formula (123) General formula (114) H H H H H H H H 980 General formula (114) General formula (114) CN Formula (123) General formula (114) H CH₃ H H H H H H 981 General formula (114) General formula (114) CN Formula (123) General formula (114) H CH₃O H H H H H H 982 General formula (114) General formula (114) CN Formula (123) General formula (114) H t-C₄H₉ H H H H H H 983 General formula (114) General formula (114) CN Formula (123) General formula (114) H Cl H H H H H H 984 General formula (114) General formula (114) CN Formula (123) General formula (114) H F H H H H H H 985 General formula (114) General formula (114) CN Formula (124) General formula (114) H H H H H H H H 986 General formula (114) General formula (114) CN Formula (124) General formula (114) H CH₃ H H H H H H 987 General formula (114) General formula (114) CN Formula (124) General formula (114) H CH₃O H H H H H H 988 General formula (114) General formula (114) CN Formula (124) General formula (114) H t-C₄H₉ H H H H H H 989 General formula (114) General formula (114) CN Formula (124) General formula (114) H Cl H H H H H H 990 General formula (114) General formula (114) CN Formula (124) General formula (114) H F H H H H H H

TABLE 6 Com- General formula (115) pound General formula (1) R⁷¹, R⁷², R⁷³, R⁷⁴, R⁷⁵, No. R¹ R² R³ R⁴ R⁵ R⁸⁰ R⁷⁹ R⁷⁸ R⁷⁷ R⁷⁶ 1001 General formula (115) General formula (115) CN General formula (115) General formula (115) H H H H H 1002 General formula (115) General formula (115) CN General formula (115) General formula (115) H CH₃ H H H 1003 General formula (115) General formula (115) CN General formula (115) General formula (115) H CH₃O H H H 1004 General formula (115) General formula (115) CN General formula (115) General formula (115) H C₆H₅ H H H 1005 General formula (115) General formula (115) CN General formula (115) General formula (115) H CH₃ H CH₃ H 1006 General formula (115) General formula (115) CN General formula (115) General formula (115) H CH₃O H CH₃O H 1007 General formula (115) General formula (115) CN General formula (115) General formula (115) H C₆H₅ H C₆H₅ H 1008 General formula (115) General formula (115) CN General formula (115) General formula (115) H H CH₃ H H 1009 General formula (115) General formula (115) CN General formula (115) General formula (115) H H CH₃O H H 1010 General formula (115) General formula (115) CN General formula (115) General formula (115) H H t-C₄H₉ H H 1011 General formula (115) General formula (115) CN General formula (115) General formula (115) H H Cl H H 1012 General formula (115) General formula (115) CN General formula (115) General formula (115) H H F H H 1013 General formula (115) General formula (115) CN General formula (115) General formula (115) H H C₆H₅ H H 1014 General formula (115) General formula (115) CN General formula (115) General formula (115) H H p-C₆H₅— H H C₆H₄ 1015 General formula (115) General formula (115) CN General formula (115) H H H H H H 1016 General formula (115) General formula (115) CN H General formula (115) H H H H H 1017 General formula (115) General formula (115) CN H H H H H H H 1018 General formula (115) H CN General formula (115) H H H H H H 1019 H General formula (115) CN General formula (115) H H H H H H 1020 General formula (115) H CN H H H H H H H 1021 General formula (115) General formula (115) CN General formula (115) F H H H H H 1022 General formula (115) General formula (115) CN F General formula (115) H H H H H 1023 General formula (115) General formula (115) CN F F H H H H H 1024 General formula (115) F CN General formula (115) F H H H H H 1025 F General formula (115) CN General formula (115) F H H H H H 1026 General formula (115) F CN F F H H H H H 1027 General formula (115) General formula (115) CN General formula (115) OH H H H H H 1028 General formula (115) General formula (115) CN OH General formula (115) H H H H H 1029 General formula (115) General formula (115) CN OH OH H H H H H 1030 General formula (115) OH CN General formula (115) OH H H H H H 1031 OH General formula (115) CN General formula (115) OH H H H H H 1032 General formula (115) OH CN OH OH H H H H H 1033 General formula (115) General formula (115) CN Cl General formula (115) H H H H H 1034 General formula (115) General formula (115) CN Cl General formula (115) H H CH₃ H H 1035 General formula (115) General formula (115) CN Cl General formula (115) H H CH₃O H H 1036 General formula (115) General formula (115) CN Cl General formula (115) H H t-C₄H₉ H H 1037 General formula (115) General formula (115) CN Cl General formula (115) H H Cl H H 1038 General formula (115) General formula (115) CN Cl General formula (115) H H F H H 1039 General formula (115) General formula (115) CN F General formula (115) H H H H H 1040 General formula (115) General formula (115) CN F General formula (115) H H CH₃ H H 1041 General formula (115) General formula (115) CN F General formula (115) H H CH₃O H H 1042 General formula (115) General formula (115) CN F General formula (115) H H t-C₄H₉ H H 1043 General formula (115) General formula (115) CN F General formula (115) H H Cl H H 1044 General formula (115) General formula (115) CN F General formula (115) H H F H H 1045 General formula (115) General formula (115) CN CH₃O General formula (115) H H H H H 1046 General formula (115) General formula (115) CN CH₃O General formula (115) H H CH₃ H H 1047 General formula (115) General formula (115) CN CH₃O General formula (115) H H CH₃O H H 1048 General formula (115) General formula (115) CN CH₃O General formula (115) H H t-C₄H₉ H H 1049 General formula (115) General formula (115) CN CH₃O General formula (115) H H Cl H H 1050 General formula (115) General formula (115) CN CH₃O General formula (115) H H F H H 1051 General formula (115) General formula (115) CN C₂H₅O General formula (115) H H H H H 1052 General formula (115) General formula (115) CN C₂H₅O General formula (115) H H CH₃ H H 1053 General formula (115) General formula (115) CN C₂H₅O General formula (115) H H CH₃O H H 1054 General formula (115) General formula (115) CN C₂H₅O General formula (115) H H t-C₄H₉ H H 1055 General formula (115) General formula (115) CN C₂H₅O General formula (115) H H Cl H H 1056 General formula (115) General formula (115) CN C₂H₅O General formula (115) H H F H H 1057 General formula (115) General formula (115) CN C₆H₅O General formula (115) H H H H H 1058 General formula (115) General formula (115) CN C₆H₅O General formula (115) H H CH₃ H H 1059 General formula (115) General formula (115) CN C₆H₅O General formula (115) H H CH₃O H H 1060 General formula (115) General formula (115) CN C₆H₅O General formula (115) H H t-C₄H₉ H H 1061 General formula (115) General formula (115) CN C₆H₅O General formula (115) H H Cl H H 1062 General formula (115) General formula (115) CN C₆H₅O General formula (115) H H F H H 1063 General formula (115) General formula (115) CN Formula (121) General formula (115) H H H H H 1064 General formula (115) General formula (115) CN Formula (121) General formula (115) H H CH₃ H H 1065 General formula (115) General formula (115) CN Formula (121) General formula (115) H H CH₃O H H 1066 General formula (115) General formula (115) CN Formula (121) General formula (115) H H t-C₄H₉ H H 1067 General formula (115) General formula (115) CN Formula (121) General formula (115) H H Cl H H 1068 General formula (115) General formula (115) CN Formula (121) General formula (115) H H F H H 1069 General formula (115) General formula (115) CN Formula (122) General formula (115) H H H H H 1070 General formula (115) General formula (115) CN Formula (122) General formula (115) H H CH₃ H H 1071 General formula (115) General formula (115) CN Formula (122) General formula (115) H H CH₃O H H 1072 General formula (115) General formula (115) CN Formula (122) General formula (115) H H t-C₄H₉ H H 1073 General formula (115) General formula (115) CN Formula (122) General formula (115) H H Cl H H 1074 General formula (115) General formula (115) CN Formula (122) General formula (115) H H F H H 1075 General formula (115) General formula (115) CN Formula (123) General formula (115) H H H H H 1076 General formula (115) General formula (115) CN Formula (123) General formula (115) H H CH₃ H H 1077 General formula (115) General formula (115) CN Formula (123) General formula (115) H H CH₃O H H 1078 General formula (115) General formula (115) CN Formula (123) General formula (115) H H t-C₄H₉ H H 1079 General formula (115) General formula (115) CN Formula (123) General formula (115) H H Cl H H 1080 General formula (115) General formula (115) CN Formula (123) General formula (115) H H F H H 1081 General formula (115) General formula (115) CN Formula (124) General formula (115) H H H H H 1082 General formula (115) General formula (115) CN Formula (124) General formula (115) H H CH₃ H H 1083 General formula (115) General formula (115) CN Formula (124) General formula (115) H H CH₃O H H 1084 General formula (115) General formula (115) CN Formula (124) General formula (115) H H t-C₄H₉ H H 1085 General formula (115) General formula (115) CN Formula (124) General formula (115) H H Cl H H 1086 General formula (115) General formula (115) CN Formula (124) General formula (115) H H F H H

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (131):

wherein in the general formula (131), from 0 to 1 of R¹ to R⁵ represents a cyano group, from 1 to 5 of R¹ to R⁵ each represent a group represented by the following general formula (132), and the balance of R¹ to R⁵ each represent a hydrogen atom or a substituent other than the above,

wherein in the general formula (132), R¹¹ to R²⁰ each independently represent a hydrogen atom or a substituent, in which R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, and R¹⁹ and R²⁰ each may be bonded to each other to form a cyclic structure; and L¹² represents a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

(2) The compound according to the item (1), wherein the group represented by the general formula (132) is a group represented by any one of the following general formulae (133) to (138):

wherein in the general formulae (133) to (138), R²¹ to R²⁴, R²⁷ to R³⁸, R⁴¹ to R⁴⁸, R⁵¹ to R⁵⁸, R⁶¹ to R⁶⁵, R⁷¹ to R⁷⁹, R⁸¹ to R⁹⁰ each independently represent a hydrogen atom or a substituent, in which R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁷ and R²⁸, R²⁸ and R²⁹, R²⁹ and R³⁰, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁴ and R⁶⁵, R⁵⁴ and R⁶¹, R⁵⁵ and R⁶⁵, R⁷¹ and R⁷², R⁷² and R⁷³, R⁷³ and R⁷⁴, R⁷⁴ and R⁷⁵, R⁷⁶ and R⁷⁷, R⁷⁷ and R⁷⁸, R⁷⁸ and R⁷⁹, R⁸¹ and R⁸², R⁸² and R⁸³, R⁸³ and R⁸⁴, R⁸⁵ and R⁸⁶, R⁸⁶ and R⁸⁷, R⁸⁷ and R⁸⁸, and R⁸⁹ and R⁹⁰ each may be bonded to each other to form a cyclic structure; and L¹³ to L¹⁸ each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

(3) The compound according to the item (1) or (2), wherein in the general formula (131), R³ represents a cyano group.

(4) The compound according to any one of the items (1) to (3), wherein in the general formula (131), R¹ and R⁴ each represent a group represented by the general formula (132).

(5) The compound according to any one of the items (1) to (4), wherein in the general formula (132), L¹² represents a phenylene group.

(6) The compound according to any one of the items (1) to (5), wherein the group represented by the general formula (132) is a group represented by the general formula (133).

(7) The compound according to the item (6), wherein in the general formula (133), L¹³ represents a 1,3-phenylene group.

(8) The compound according to any one of the items (1) to (5), wherein the group represented by the general formula (132) is a group represented by the general formula (134).

(9) The compound according to the item (8), wherein in the general formula (134), L¹⁴ represents a 1,4-phenylene group.

(10) The compound according to any one of the items (1) to (5), wherein the group represented by the general formula (132) is a group represented by the general formula (138).

(11) The compound according to the item (10), wherein in the general formula (138), L¹⁸ represents a 1,4-phenylene group.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include compounds represented by the following general formula (141). The entire description of WO 2013/011954 including the paragraphs 0007 to 0047 and 0073 to 0085 is incorporated herein by reference.

wherein in the general formula (141), R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and R¹⁷ each independently represent a hydrogen atom or an electron donating group, provided that at least one thereof represents an electron donating group; R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independently represent a hydrogen atom or an electron withdrawing group having no unshared electron pair at the α-position; and Z represents a single bond or >C═Y, wherein Y represents O, S, C(CN)₂ or C(COOH)₂, provided that when Z represents a single bond, at least one of R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ represents an electron withdrawing group having no unshared electron pair at the α-position.

Specific examples of the compounds include the compounds shown in the following tables. In the tables, D1 to D3 represent the following aryl groups substituted with an electron donating group, respectively; A1 to A5 represent the following electron withdrawing groups, respectively; H represents a hydrogen atom; and Ph represents a phenyl group.

TABLE 7 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2001 H H A1 A1 Ph single bond H 2002 H D1 A1 A1 Ph single bond H 2003 H D2 A1 A1 Ph single bond H 2004 H D3 A1 A1 Ph single bond H 2005 H H A2 A2 Ph single bond H 2006 H D1 A2 A2 Ph single bond H 2007 H D2 A2 A2 Ph single bond H 2008 H D3 A2 A2 Ph single bond H 2009 H H A3 A3 Ph single bond H 2010 H D1 A3 A3 Ph single bond H 2011 H D2 A3 A3 Ph single bond H 2012 H D3 A3 A3 Ph single bond H 2013 H H A4 A4 Ph single bond H 2014 H D1 A4 A4 Ph single bond H 2015 H D2 A4 A4 Ph single bond H 2016 H D3 A4 A4 Ph single bond H 2017 H H A5 A5 Ph single bond H 2018 H D1 A5 A5 Ph single bond H 2019 H D2 A5 A5 Ph single bond H 2020 H D3 A5 A5 Ph single bond H 2021 D1 D1 A1 A1 Ph single bond H 2022 D2 D2 A1 A1 Ph single bond H 2023 D3 D3 A1 A1 Ph single bond H 2024 D1 D1 A2 A2 Ph single bond H 2025 D2 D2 A2 A2 Ph single bond H 2026 D3 D3 A2 A2 Ph single bond H 2027 D1 D1 A3 A3 Ph single bond H 2028 D2 D2 A3 A3 Ph single bond H 2029 D3 D3 A3 A3 Ph single bond H 2030 D1 D1 A4 A4 Ph single bond H 2031 D2 D2 A4 A4 Ph single bond H 2032 D3 D3 A4 A4 Ph single bond H 3033 D1 D1 A5 A5 Ph single bond H 2034 D2 D2 A5 A5 Ph single bond H 2035 D3 D3 A5 A5 Ph single bond H

TABLE 8 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2036 H H H A1 Ph single bond H 2037 H D1 H A1 Ph single bond H 2038 H D2 H A1 Ph single bond H 2039 H D3 H A1 Ph single bond H 2040 H H H A2 Ph single bond H 2041 H D1 H A2 Ph single bond H 2042 H D2 H A2 Ph single bond H 2043 H D3 H A2 Ph single bond H 2044 H H H A3 Ph single bond H 2045 H D1 H A3 Ph single bond H 2046 H D2 H A3 Ph single bond H 2047 H D3 H A3 Ph single bond H 2048 H H H A4 Ph single bond H 2049 H D1 H A4 Ph single bond H 2050 H D2 H A4 Ph single bond H 2051 H D3 H A4 Ph single bond H 2052 H H H A5 Ph single bond H 2053 H D1 H A5 Ph single bond H 2054 H D2 H A5 Ph single bond H 2055 H D3 H A5 Ph single bond H 2056 D1 D1 H A1 Ph single bond H 2057 D2 D2 H A1 Ph single bond H 2058 D3 D3 H A1 Ph single bond H 2059 D1 D1 H A2 Ph single bond H 2060 D2 D2 H A2 Ph single bond H 2061 D3 D3 H A2 Ph single bond H 2062 D1 D1 H A3 Ph single bond H 2063 D2 D2 H A3 Ph single bond H 2064 D3 D3 H A3 Ph single bond H 2065 D1 D1 H A4 Ph single bond H 2066 D2 D2 H A4 Ph single bond H 2067 D3 D3 H A4 Ph single bond H 2068 D1 D1 H A5 Ph single bond H 2069 D2 D2 H A5 Ph single bond H 2070 D3 D3 H A5 Ph single bond H

TABLE 9 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2071 H H A1 A1 Ph C═O H 2072 H D1 A1 A1 Ph C═O H 2073 H D2 A1 A1 Ph C═O H 2074 H D3 A1 A1 Ph C═O H 2075 H H A2 A2 Ph C═O H 2076 H D1 A2 A2 Ph C═O H 2077 H D2 A2 A2 Ph C═O H 2078 H D3 A2 A2 Ph C═O H 2079 H H A3 A3 Ph C═O H 2080 H D1 A3 A3 Ph C═O H 2081 H D2 A3 A3 Ph C═O H 2082 H D3 A3 A3 Ph C═O H 2083 H H A4 A4 Ph C═O H 2084 H D1 A4 A4 Ph C═O H 2085 H D2 A4 A4 Ph C═O H 2086 H D3 A4 A4 Ph C═O H 2087 H H A5 A5 Ph C═O H 2088 H D1 A5 A5 Ph C═O H 2089 H D2 A5 A5 Ph C═O H 2090 H D3 A5 A5 Ph C═O H 2091 D1 D1 A1 A1 Ph C═O H 2092 D2 D2 A1 A1 Ph C═O H 2093 D3 D3 A1 A1 Ph C═O H 2094 D1 D1 A2 A2 Ph C═O H 2095 D2 D2 A2 A2 Ph C═O H 2096 D3 D3 A2 A2 Ph C═O H 2097 D1 D1 A3 A3 Ph C═O H 2098 D2 D2 A3 A3 Ph C═O H 2099 D3 D3 A3 A3 Ph C═O H 2100 D1 D1 A4 A4 Ph C═O H 2101 D2 D2 A4 A4 Ph C═O H 2102 D3 D3 A4 A4 Ph C═O H 2103 D1 D1 A5 A5 Ph C═O H 2104 D2 D2 A5 A5 Ph C═O H 2105 D3 D3 A5 A5 Ph C═O H

TABLE 10 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2106 H H H A1 Ph C═O H 2107 H D1 H A1 Ph C═O H 2108 H D2 H A1 Ph C═O H 2109 H D3 H A1 Ph C═O H 2110 H H H A2 Ph C═O H 2111 H D1 H A2 Ph C═O H 2112 H D2 H A2 Ph C═O H 2113 H D3 H A2 Ph C═O H 2114 H H H A3 Ph C═O H 2115 H D1 H A3 Ph C═O H 2116 H D2 H A3 Ph C═O H 2117 H D3 H A3 Ph C═O H 2118 H H H A4 Ph C═O H 2119 H D1 H A4 Ph C═O H 2120 H D2 H A4 Ph C═O H 2121 H D3 H A4 Ph C═O H 2122 H H H A5 Ph C═O H 2123 H D1 H A5 Ph C═O H 2124 H D2 H A5 Ph C═O H 2125 H D3 H A5 Ph C═O H 2126 D1 D1 H A1 Ph C═O H 2127 D2 D2 H A1 Ph C═O H 2128 D3 D3 H A1 Ph C═O H 2129 D1 D1 H A2 Ph C═O H 2130 D2 D2 H A2 Ph C═O H 2131 D3 D3 H A2 Ph C═O H 2132 D1 D1 H A3 Ph C═O H 2133 D2 D2 H A3 Ph C═O H 2134 D3 D3 H A3 Ph C═O H 2135 D1 D1 H A4 Ph C═O H 2136 D2 D2 H A4 Ph C═O H 2137 D3 D3 H A4 Ph C═O H 2138 D1 D1 H A5 Ph C═O H 2139 D2 D2 H A5 Ph C═O H 2140 D3 D3 H A5 Ph C═O H 2141 H H H H Ph C═O H

TABLE 11 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2142 H H A1 A1 Ph C═S H 2143 H D1 A1 A1 Ph C═S H 2144 H D2 A1 A1 Ph C═S H 2145 H D3 A1 A1 Ph C═S H 2146 H H A2 A2 Ph C═S H 2147 H D1 A2 A2 Ph C═S H 2148 H D2 A2 A2 Ph C═S H 2149 H D3 A2 A2 Ph C═S H 2150 H H A3 A3 Ph C═S H 2151 H D1 A3 A3 Ph C═S H 2152 H D2 A3 A3 Ph C═S H 2153 H D3 A3 A3 Ph C═S H 2154 H H A4 A4 Ph C═S H 2155 H D1 A4 A4 Ph C═S H 2156 H D2 A4 A4 Ph C═S H 2157 H D3 A4 A4 Ph C═S H 2158 H H A5 A5 Ph C═S H 2159 H D1 A5 A5 Ph C═S H 2160 H D2 A5 A5 Ph C═S H 2161 H D3 A5 A5 Ph C═S H 2162 D1 D1 A1 A1 Ph C═S H 2163 D2 D2 A1 A1 Ph C═S H 2164 D3 D3 A1 A1 Ph C═S H 2165 D1 D1 A2 A2 Ph C═S H 2166 D2 D2 A2 A2 Ph C═S H 2167 D3 D3 A2 A2 Ph C═S H 2168 D1 D1 A3 A3 Ph C═S H 2169 D2 D2 A3 A3 Ph C═S H 2170 D3 D3 A3 A3 Ph C═S H 2171 D1 D1 A4 A4 Ph C═S H 2172 D2 D2 A4 A4 Ph C═S H 2173 D3 D3 A4 A4 Ph C═S H 2174 D1 D1 A5 A5 Ph C═S H 2175 D2 D2 A5 A5 Ph C═S H 2176 D3 D3 A5 A5 Ph C═S H

TABLE 12 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2177 H H H A1 Ph C═S H 2178 H D1 H A1 Ph C═S H 2179 H D2 H A1 Ph C═S H 2180 H D3 H A1 Ph C═S H 2181 H H H A2 Ph C═S H 2182 H D1 H A2 Ph C═S H 2183 H D2 H A2 Ph C═S H 2184 H D3 H A2 Ph C═S H 2185 H H H A3 Ph C═S H 2186 H D1 H A3 Ph C═S H 2187 H D2 H A3 Ph C═S H 2188 H D3 H A3 Ph C═S H 2189 H H H A4 Ph C═S H 2190 H D1 H A4 Ph C═S H 2191 H D2 H A4 Ph C═S H 2192 H D3 H A4 Ph C═S H 2193 H H H A5 Ph C═S H 2194 H D1 H A5 Ph C═S H 2195 H D2 H A5 Ph C═S H 2196 H D3 H A5 Ph C═S H 2197 D1 D1 H A1 Ph C═S H 2198 D2 D2 H A1 Ph C═S H 2199 D3 D3 H A1 Ph C═S H 2200 D1 D1 H A2 Ph C═S H 2201 D2 D2 H A2 Ph C═S H 2202 D3 D3 H A2 Ph C═S H 2203 D1 D1 H A3 Ph C═S H 2204 D2 D2 H A3 Ph C═S H 2205 D3 D3 H A3 Ph C═S H 2206 D1 D1 H A4 Ph C═S H 2207 D2 D2 H A4 Ph C═S H 2208 D3 D3 H A4 Ph C═S H 2209 D1 D1 H A5 Ph C═S H 2210 D2 D2 H A5 Ph C═S H 2211 D3 D3 H A5 Ph C═S H 2212 H H H H Ph C═S H

TABLE 13 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2213 H H A1 A1 Ph C═C (CN) ₂ H 2214 H D1 A1 A1 Ph C═C (CN) ₂ H 2215 H D2 A1 A1 Ph C═C (CN) ₂ H 2216 H D3 A1 A1 Ph C═C (CN) ₂ H 2217 H H A2 A2 Ph C═C (CN) ₂ H 2218 H D1 A2 A2 Ph C═C (CN) ₂ H 2219 H D2 A2 A2 Ph C═C (CN) ₂ H 2220 H D3 A2 A2 Ph C═C (CN) ₂ H 2221 H H A3 A3 Ph C═C (CN) ₂ H 2222 H D1 A3 A3 Ph C═C (CN) ₂ H 2223 H D2 A3 A3 Ph C═C (CN) ₂ H 2224 H D3 A3 A3 Ph C═C (CN) ₂ H 2225 H H A4 A4 Ph C═C (CN) ₂ H 2226 H D1 A4 A4 Ph C═C (CN) ₂ H 2227 H D2 A4 A4 Ph C═C (CN) ₂ H 2228 H D3 A4 A4 Ph C═C (CN) ₂ H 2229 H H A5 A5 Ph C═C (CN) ₂ H 2230 H D1 A5 A5 Ph C═C (CN) ₂ H 2231 H D2 A5 A5 Ph C═C (CN) ₂ H 2232 H D3 A5 A5 Ph C═C (CN) ₂ H 2233 D1 D1 A1 A1 Ph C═C (CN) ₂ H 2234 D2 D2 A1 A1 Ph C═C (CN) ₂ H 2235 D3 D3 A1 A1 Ph C═C (CN) ₂ H 2236 D1 D1 A2 A2 Ph C═C (CN) ₂ H 2237 D2 D2 A2 A2 Ph C═C (CN) ₂ H 2238 D3 D3 A2 A2 Ph C═C (CN) ₂ H 2239 D1 D1 A3 A3 Ph C═C (CN) ₂ H 2240 D2 D2 A3 A3 Ph C═C (CN) ₂ H 2241 D3 D3 A3 A3 Ph C═C (CN) ₂ H 2242 D1 D1 A4 A4 Ph C═C (CN) ₂ H 2243 D2 D2 A4 A4 Ph C═C (CN) ₂ H 2244 D3 D3 A4 A4 Ph C═C (CN) ₂ H 2245 D1 D1 A5 A5 Ph C═C (CN) ₂ H 2246 D2 D2 A5 A5 Ph C═C (CN) ₂ H 2247 D3 D3 A5 A5 Ph C═C (CN) ₂ H

TABLE 14 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2248 H H H A1 Ph C═C (CN) ₂ H 2249 H D1 H A1 Ph C═C (CN) ₂ H 2250 H D2 H A1 Ph C═C (CN) ₂ H 2251 H D3 H A1 Ph C═C (CN) ₂ H 2252 H H H A2 Ph C═C (CN) ₂ H 2253 H D1 H A2 Ph C═C (CN) ₂ H 2254 H D2 H A2 Ph C═C (CN) ₂ H 2255 H D3 H A2 Ph C═C (CN) ₂ H 2256 H H H A3 Ph C═C (CN) ₂ H 2257 H D1 H A3 Ph C═C (CN) ₂ H 2258 H D2 H A3 Ph C═C (CN) ₂ H 2259 H D3 H A3 Ph C═C (CN) ₂ H 2260 H H H A4 Ph C═C (CN) ₂ H 2261 H D1 H A4 Ph C═C (CN) ₂ H 2262 H D2 H A4 Ph C═C (CN) ₂ H 2263 H D3 H A4 Ph C═C (CN) ₂ H 2264 H H H A5 Ph C═C (CN) ₂ H 2265 H D1 H A5 Ph C═C (CN) ₂ H 2266 H D2 H A5 Ph C═C (CN) ₂ H 2267 H D3 H A5 Ph C═C (CN) ₂ H 2268 D1 D1 H A1 Ph C═C (CN) ₂ H 2269 D2 D2 H A1 Ph C═C (CN) ₂ H 2270 D3 D3 H A1 Ph C═C (CN) ₂ H 2271 D1 D1 H A2 Ph C═C (CN) ₂ H 2272 D2 D2 H A2 Ph C═C (CN) ₂ H 2273 D3 D3 H A2 Ph C═C (CN) ₂ H 2274 D1 D1 H A3 Ph C═C (CN) ₂ H 2275 D2 D2 H A3 Ph C═C (CN) ₂ H 2276 D3 D3 H A3 Ph C═C (CN) ₂ H 2277 D1 D1 H A4 Ph C═C (CN) ₂ H 2278 D2 D2 H A4 Ph C═C (CN) ₂ H 2279 D3 D3 H A4 Ph C═C (CN) ₂ H 2280 D1 D1 H A5 Ph C═C (CN) ₂ H 2281 D2 D2 H A5 Ph C═C (CN) ₂ H 2282 D3 D3 H A5 Ph C═C (CN) ₂ H 2283 H H H H Ph C═C (CN) ₂ H

TABLE 15 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2284 H H A1 A1 Ph C═C (COOH) ₂ H 2285 H D1 A1 A1 Ph C═C (COOH) ₂ H 2286 H D2 A1 A1 Ph C═C (COOH) ₂ H 2287 H D3 A1 A1 Ph C═C (COOH) ₂ H 2288 H H A2 A2 Ph C═C (COOH) ₂ H 2289 H D1 A2 A2 Ph C═C (COOH) ₂ H 2290 H D2 A2 A2 Ph C═C (COOH) ₂ H 2291 H D3 A2 A2 Ph C═C (COOH) ₂ H 2292 H H A3 A3 Ph C═C (COOH) ₂ H 2293 H D1 A3 A3 Ph C═C (COOH) ₂ H 2294 H D2 A3 A3 Ph C═C (COOH) ₂ H 2295 H D3 A3 A3 Ph C═C (COOH) ₂ H 2296 H H A4 A4 Ph C═C (COOH) ₂ H 2297 H D1 A4 A4 Ph C═C (COOH) ₂ H 2298 H D2 A4 A4 Ph C═C (COOH) ₂ H 2299 H D3 A4 A4 Ph C═C (COOH) ₂ H 2300 H H A5 A5 Ph C═C (COOH) ₂ H 2301 H D1 A5 A5 Ph C═C (COOH) ₂ H 2302 H D2 A5 A5 Ph C═C (COOH) ₂ H 2303 H D3 A5 A5 Ph C═C (COOH) ₂ H 2304 D1 D1 A1 A1 Ph C═C (COOH) ₂ H 2305 D2 D2 A1 A1 Ph C═C (COOH) ₂ H 2306 D3 D3 A1 A1 Ph C═C (COOH) ₂ H 2307 D1 D1 A2 A2 Ph C═C (COOH) ₂ H 2308 D2 D2 A2 A2 Ph C═C (COOH) ₂ H 2309 D3 D3 A2 A2 Ph C═C (COOH) ₂ H 2310 D1 D1 A3 A3 Ph C═C (COOH) ₂ H 2311 D2 D2 A3 A3 Ph C═C (COOH) ₂ H 2312 D3 D3 A3 A3 Ph C═C (COOH) ₂ H 2313 D1 D1 A4 A4 Ph C═C (COOH) ₂ H 2314 D2 D2 A4 A4 Ph C═C (COOH) ₂ H 2315 D3 D3 A4 A4 Ph C═C (COOH) ₂ H 2316 D1 D1 A5 A5 Ph C═C (COOH) ₂ H 2317 D2 D2 A5 A5 Ph C═C (COOH) ₂ H 2318 D3 D3 A5 A5 Ph C═C (COOH) ₂ H

TABLE 16 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2319 H H H A1 Ph C═C (COOH) ₂ H 2320 H D1 H A1 Ph C═C (COOH) ₂ H 2321 H D2 H A1 Ph C═C (COOH) ₂ H 2322 H D3 H A1 Ph C═C (COOH) ₂ H 2323 H H H A2 Ph C═C (COOH) ₂ H 2324 H D1 H A2 Ph C═C (COOH) ₂ H 2325 H D2 H A2 Ph C═C (COOH) ₂ H 2326 H D3 H A2 Ph C═C (COOH) ₂ H 2327 H H H A3 Ph C═C (COOH) ₂ H 2328 H D1 H A3 Ph C═C (COOH) ₂ H 2329 H D2 H A3 Ph C═C (COOH) ₂ H 2330 H D3 H A3 Ph C═C (COOH) ₂ H 2331 H H H A4 Ph C═C (COOH) ₂ H 2332 H D1 H A4 Ph C═C (COOH) ₂ H 2333 H D2 H A4 Ph C═C (COOH) ₂ H 2334 H D3 H A4 Ph C═C (COOH) ₂ H 2335 H H H A5 Ph C═C (COOH) ₂ H 2336 H D1 H A5 Ph C═C (COOH) ₂ H 2337 H D2 H A5 Ph C═C (COOH) ₂ H 2338 H D3 H A5 Ph C═C (COOH) ₂ H 2339 D1 D1 H A1 Ph C═C (COOH) ₂ H 2340 D2 D2 H A1 Ph C═C (COOH) ₂ H 2341 D3 D3 H A1 Ph C═C (COOH) ₂ H 2342 D1 D1 H A2 Ph C═C (COOH) ₂ H 2343 D2 D2 H A2 Ph C═C (COOH) ₂ H 2344 D3 D3 H A2 Ph C═C (COOH) ₂ H 2345 D1 D1 H A3 Ph C═C (COOH) ₂ H 2346 D2 D2 H A3 Ph C═C (COOH) ₂ H 2347 D3 D3 H A3 Ph C═C (COOH) ₂ H 2348 D1 D1 H A4 Ph C═C (COOH) ₂ H 2349 D2 D2 H A4 Ph C═C (COOH) ₂ H 2350 D3 D3 H A4 Ph C═C (COOH) ₂ H 2351 D1 D1 H A5 Ph C═C (COOH) ₂ H 2352 D2 D2 H A5 Ph C═C (COOH) ₂ H 2353 D3 D3 H A5 Ph C═C (COOH) ₂ H 2354 H H H H Ph C═C (COOH) ₂ H

Examples of the preferred light-emitting material include compounds represented by the following general formula (151). The entire description of WO 2013/011955 including the paragraphs 0007 to 0033 and 0059 to 0066 is incorporated herein by reference.

wherein in the general formula (151), R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ each independently represent a hydrogen atom or an electron donating group, provided that at least one thereof represents an electron donating group; R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independently represent a hydrogen atom or an electron withdrawing group, provided that at least one thereof represents an electron withdrawing group.

Specific examples of the compounds include the compounds shown in the following tables. In the tables, D1 to D10 represent the unsubstituted electron donating groups having the following structures, respectively.

TABLE 17

  Compound 3001 Compound No. R² R⁷ R¹⁰ R¹⁵ Other Rs 3002  D1  D1 CN CN H 3003  D2  D2 CN CN H 3004  D3  D3 CN CN H 3005  D4  D4 CN CN H 3006  D5  D5 CN CN H 3007  D6  D6 CN CN H 3008  D7  D7 CN CN H 3009  D8  D8 CN CN H 3010  D9  D9 CN CN H 3011 D10 D10 CN CN H 3012 H  D1 H CN H 3013 H  D2 H CN H 3014 H  D3 H CN H 3015 H  D4 H CN H 3016 H  D5 H CN H 3017 H  D6 H CN H 3018 H  D7 H CN H 3019 H  D8 H CN H 3020 H  D9 H CN H 3021 H D10 H CN H

TABLE 18 Compound Other No. R³ R⁶ R¹¹ R¹⁴ Rs 3022 D1 D1 CN CN H 3023 D2 D2 CN CN H 3024 D3 D3 CN CN H 3025 D4 D4 CN CN H 3026 D5 D5 CN CN H 3027 D6 D6 CN CN H 3028 D7 D7 CN CN H 3029 D8 D8 CN CN H 3030 D9 D9 CN CN H 3031 D10 D10 CN CN H 3032 H D1 H CN H 3033 H D2 H CN H 3034 H D3 H CN H 3035 H D4 H CN H 3036 H D5 H CN H 3037 H D6 H CN H 3038 H D7 H CN H 3039 H D8 H CN H 3040 H D9 H CN H 3041 H D10 H CN H

TABLE 19 Compound Other No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Rs 3042 diphenylamino group H CN H H 3043 bis (2-methylphenyl) amino group H CN H H 3044 bis (3-methylphenyl) amino group H CN H H 3045 bis (2,4-dimethylphenyl) amino group H CN H H 3046 bis (2,6-dimethylphenyl) amino group H CN H H 3047 bis (3,5-dimethylphenyl) amino group H CN H H 3048 bis (2,4,6-trimethylphenyl) amino group H CN H H 3049 bis (4-ethylphenyl) amino group H CN H H 3050 bis (4-propylphenyl) amino group H CN H H 3051 diphenylamino group H H CN H 3052 bis (2-methylphenyl) amino group H H CN H 3053 bis (3-methylphenyl) amino group H H CN H 3054 bis (4-methylphenyl) amino group H H CN H 3055 bis (2,4-dimethylphenyl) amino group H H CN H 3056 bis (2,6-dimethylphenyl) amino group H H CN H 3057 bis (3,5-dimethylphenyl) amino group H H CN H 3058 bis (2,4,6-trimethylphenyl) amino group H H CN H 3059 bis (4-ethylphenyl) amino group H H CN H 3060 bis (4-propylphenyl) amino group H H CN H

TABLE 20 Compound Other No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Rs 3061 H diphenylamino group CN H H 3062 H bis (2-methylphenyl) amino group CN H H 3063 H bis (3-methylphenyl) amino group CN H H 3064 H bis (4-methylphenyl) amino group CN H H 3065 H bis (2,4-dimethylphenyl) amino group CN H H 3066 H bis (2,6-dimethylphenyl) amino group CN H H 3067 H bis (3,5-dimethylphenyl) amino group CN H H 3068 H bis (2,4,6-trimethylphenyl) amino group CN H H 3069 H bis (4-ethylphenyl) amino group CN H H 3070 H bis (4-propylphenyl) amino group CN H H 3071 H diphenylamino group H CN H 3072 H bis (2-methylphenyl) amino group H CN H 3073 H bis (3-methylphenyl) amino group H CN H 3074 H bis (4-methylphenyl) amino group H CN H 3075 H bis (2,4-dimethylphenyl) amino group H CN H 3076 H bis (2,6-dimethylphenyl) amino group H CN H 3077 H bis (3,5-dimethylphenyl) amino group H CN H 3078 H bis (2,4,6-trimethylphenyl) amino group H CN H 3079 H bis (4-ethylphenyl) amino group H CN H 3080 H bis (4-propylphenyl) amino group H CN H

Examples of the preferred light-emitting material include compounds represented by the following general formula (161). The entire description of WO 2013/081088 including the paragraphs 0008 to 0071 and 0118 to 0133 is incorporated herein by reference.

wherein in the general formula (161), any two or Y¹, Y² and Y³ each represent a nitrogen atom, and the balance thereof represents a methine group, or all Y¹, Y² and Y³ each represent a nitrogen atom; Z¹ and Z² each independently represent a hydrogen atom or a substituent; and R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group or a substituted or unsubstituted carbazolyl group. The compound represented by the general formula (161) has at least two carbazole structures in the molecule thereof.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include compounds represented by the following general formula (171). The entire description of JP-A-2013-256490 including the paragraphs 0009 to 0046 and 0093 to 0134 is incorporated herein by reference.

wherein in the general formula (171), Ar¹ to Ar³ each independently represent a substituted or unsubstituted aryl group, provided that at least one thereof represents an aryl group substituted with a group represented by the following general formula (172).

wherein in the general formula (172), R¹ to R⁸ each independently represent a hydrogen atom or a substituent; Z represents O, S, O═C, or Ar⁴—N; and Ar⁴ represents a substituted or unsubstituted aryl group, provided that R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each may be bonded to each other to form a cyclic structure.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include compounds represented by the following general formula (181). The entire description of JP-A-2013-116975 including the paragraphs 0008 to 0020 and 0038 to 0040 is incorporated herein by reference.

wherein in the general formula (181), R¹, R², R⁴ to R⁸, R¹¹, R¹² and R¹⁴ to R¹⁸ each independently represent a hydrogen atom or a substituent.

Examples of the compound include the following compound.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (191):

wherein in the general formula (191), Ar¹ represents a substituted or unsubstituted arylene group; Ar² and Ar³ each independently represent a substituted or unsubstituted aryl group; and R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group, and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each may be bonded to each other to form a cyclic structure.

(2) The compound according to the item (1), wherein in the general formula (191), at least one of R¹ to R⁴ represents a substituted or unsubstituted diarylamino group, and at least one of R⁵ to R⁸ represents a substituted or unsubstituted diarylamino group.

(3) The compound according to the item (2), wherein in the general formula (191), R³ and R⁶ each represent a substituted or unsubstituted diarylamino group.

(4) The compound according to any one of the items (1) to (3), wherein in the general formula (191), at least one of R¹ to R⁸ represents a substituted or unsubstituted diphenylamino group.

(5) The compound according to any one of the items (1) to (4), wherein in the general formula (191), Ar² and Ar³ each independently represent a substituted or unsubstituted phenyl group.

(6) The compound according to any one of the items (1) to (5), wherein in the general formula (191), Ar¹ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthracenylene group.

(7) The compound according to the item (1), wherein the compound has a structure represented by the following general formula (192):

wherein in the general formula (192), R¹ to R⁸ and R¹¹ to R²⁴ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group, and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ and R²⁰, R²¹ and R²², and R²³ and R²⁴ each may be bonded to each other to form a cyclic structure.

(8) The compound according to the item (7), wherein in the general formula (192), at least one of R¹ to R⁴ represents a substituted or unsubstituted diarylamino group, and at least one of R⁵ to R⁸ represents a substituted or unsubstituted diarylamino group.

(9) The compound according to the item (8), wherein in the general formula (192), R³ and R⁶ each represent a substituted or unsubstituted diarylamino group.

Specific examples of the compound include the following compounds. Ph represents a phenyl group.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (201):

wherein in the general formula (201), R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted carbazolyl group; and Ar¹ to Ar³ each independently represent a substituted or unsubstituted aromatic ring or a heteroaromatic ring.

(2) The compound according to the item (1), wherein in the general formula (201), at least one of R³ and R⁶ represents a substituted or unsubstituted carbazolyl group.

(3) The compound according to the item (1) or (2), wherein the carbazolyl group is a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group or a 4-carbazolyl group.

(4) The compound according to any one of the items (1) to (3), wherein the carbazolyl group has a substituent on the nitrogen atom in the carbazole ring structure.

(5) The compound according to any one of the items (1) to (4), wherein in the general formula (201), at least one of Ar¹, Ar² and Ar³ represents a benzene ring or a naphthalene ring.

(6) The compound according to any one of the items (1) to (5), wherein in the general formula (201), Ar¹, Ar² and Ar³ each represent the same aromatic ring or the same heteroaromatic ring.

(7) The compound according to any one of the items (1) to (6), wherein in the general formula (201), Ar¹, Ar² and Ar³ each represent a benzene ring.

Specific examples of the compound include the following compounds.

Examples of the preferred light-emitting material include compounds represented by the following general formulae (211) and (212). The entire description of WO 2013/133359 including the paragraphs 0007 to 0032 and 0079 to 0084 is incorporated herein by reference.

General Formula (211)

wherein in the general formula (211), Z¹, Z² and Z³ each independently represent a substituent.

wherein in the general formula (212), Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ each independently represent a substituted or unsubstituted aryl group.

Specific examples of the compound represented by the general formula (212) include the compound represented by the following structural formula.

Specific examples of the compound represented by the general formula (212) include the compounds shown in the following table. In the compounds shown in the table, Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are the same as each other, and are expressed by Ar.

TABLE 21 Compound No. Ar 4002 4-fluorophenyl 4003 3-fluorophenyl 4004 2-fluorophenyl 4005 3,5-difluorophenyl 4006 2,4,6-trifluorophenyl 4007 4-methylphenyl 4008 3-methylphenyl 4009 2-methylphenyl 4010 3,5-dimethylphenyl 4011 2,4,6-trimethylphenyl 4012 4-ethylphenyl 4013 3-ethylphenyl 4014 2-ethylphenyl 4015 3,5-diethylphenyl 4016 4-propylphenyl 4017 3-propylphenyl 4018 3,5-dipropylphenyl 4019 4-tert-butylphenyl 4020 3-tert-butylphenyl 4021 3,5-di-tert-butylphenyl 4022 1-naphthyl 4023 2-naphthyl

Examples of the preferred light-emitting material include compounds represented by the following general formula (221). The entire description of WO 2013/161437 including the paragraphs 0008 to 0054 and 0101 to 0121 is incorporated herein by reference.

wherein in the general formula (221), R¹ to R¹⁰ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R¹⁰ represents a substituted or unsubstituted aryl group, a substituted or unsubstituted diarylamino group or a substituted or unsubstituted 9-carbazolyl group, and R¹ and R², R² and R³, R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R⁸ and R⁹, and R⁹ and R¹⁰ each may be bonded to each other to form a cyclic structure.

Specific examples of the compound include the following compounds.

Examples of the preferred light-emitting material include compounds represented by the following general formula (231). The entire description of JP-A-2014-9352 including the paragraphs 0007 to 0041 and 0060 to 0069 is incorporated herein by reference.

wherein in the general formula (231), R¹ to R⁴ each independently represent a hydrogen atom or a substituted or unsubstituted (N,N-diarylamino)aryl group, provided that at least one of R¹ to R⁴ represents a substituted or unsubstituted (N,N-diarylamino)aryl group, and two aryl groups constituting the diarylamino moiety of the (N,N-diarylamino)aryl group may be bonded to each other; W¹, W², X¹, X², Y¹, Y², Z¹ and Z² each independently represent a carbon atom or a nitrogen atom; and m¹ to m⁴ each independently represent 0, 1 or 2.

Specific examples of the compound include the following compounds.

Examples of the preferred light-emitting material include compounds represented by the following general formula (241). The entire description of JP-A-2014-9224 including the by reference.

wherein in the general formula (241), R¹ to R⁶ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁶ represents a substituted or unsubstituted (N, N-diarylamino)aryl group, and two aryl groups constituting the diarylamino moiety of the (N,N-diarylamino)aryl group may be bonded to each other; X¹ to X⁶ and Y¹ to Y⁶ each independently represent a carbon atom or a nitrogen atom; and n¹, n², p¹, p², q¹ and q² each independently represent 0, 1 or 2.

Specific examples of the compound include the following compounds.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (251):

wherein in the general formula (251), one of A¹ to A⁷ represents N, and the balance each independently represent C—R; R represents a non-aromatic group; Ar¹ to Ar³ each independently represent a substituted or unsubstituted arylene group; and Z represents a single bond or a linking group.

(2) The compound according to the item (1), wherein the compound represented by the general formula (251) has a structure represented by the following general formula (252):

wherein in the general formula (252), one of A¹ to A⁷ represents N, and the balance each independently represent C—R; R represents a non-aromatic group; Ar¹ represents a substituted or unsubstituted arylene group; R¹¹ to R¹⁴ and R¹⁷ to R²⁰ each independently represent a hydrogen atom or a substituent, in which R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, and R¹⁹ and R²⁰ each may be bonded to each other to form a cyclic structure; and Z¹ represents a single bond or a linking group having 1 or 2 linking chain atoms.

(3) The compound according to the item (1), wherein the compound represented by the general formula (251) has a structure represented by the following general formula (253):

wherein in the general formula (253), from 2 to 4 of A¹ to A⁷ represent N, and the balance represent C—R; R represents a non-aromatic group; Ar¹ represents a substituted or unsubstituted arylene group; and Y represents a substituted or unsubstituted carbazol-9-yl group, a substituted or unsubstituted 10H-phenoxazin-10-yl group, a substituted or unsubstituted 10H-phenothiazin-10-yl group, or a substituted or unsubstituted 10H-phenazin-5-yl group.

(4) The compound according to the item (3), wherein in the general formula (253), Y represents a group represented by any one of the following general formulae (254) to (257):

wherein in the general formulae (254) to (257), R²¹ to R²⁴, R²⁷ to R³⁸, R⁴¹ to R⁴⁸, R⁵¹ to R⁵⁸, and R⁶¹ to R⁶⁵ each independently represent a hydrogen atom or a substituent, in which R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁷ and R²⁸, R²⁸ and R²⁹, R²⁹ and R³⁰, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁴ and R⁶⁵, R⁵⁴ and R⁶¹, and R⁵⁵ and R⁶⁵ each may be bonded to each other to form a cyclic structure.

(5) The compound according to the item (3), wherein in the general formula (253), Y represents a group represented by the following general formula (258):

wherein in the general formula (258), R^(21′) to R^(24′) and R^(27′) to R^(30′) each independently represent a hydrogen atom or a substituent, provided that at least one of R^(23′) and R^(28′) represents a substituent, and R^(21′) and R^(22′), R^(22′) and R^(23′), R^(23′) and R^(24′), R^(27′) and R^(28′), R^(28′) and R^(29′), and R^(29′) and R^(30′) each may be bonded to each other to form a cyclic structure.

(6) The compound according to the item (5), wherein in the general formula (258), at least one of R^(23′) and R^(28′) represents a substituted or unsubstituted diarylamino group or a substituted or unsubstituted carbazol-9-yl group.

(7) The compound according to the item (4), wherein in the general formula (253), Y represents a group represented by the general formula (255).

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (261):

wherein in the general formula (261), X represents an oxygen atom or a sulfur atom; and R1 to R8 each independently represent a hydrogen atom or a substituent, provided that at least one of R1 to R8 each independently represent a group represented by any of the following formulae (262) to (266), and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸ each may be bonded to each other to form a cyclic structure.

wherein in the general formulae (262) to (266), L²⁰, L³⁰, L⁴⁰, L⁵⁰, and L⁶⁰ each independently represent a single bond or a divalent linking group, and the group is bonded to the cyclic structure of the general formula (261) through L²⁰, L³⁰, L⁴⁰, L⁵⁰, and L⁶⁰; and R²¹ to R²⁸, R³¹ to R³⁸, R^(3a), R^(3b), R⁴¹ to R⁴⁸, R^(4a), R⁵¹ to R⁵⁸, and R⁶¹ to R⁶⁸ each independently represent a hydrogen atom or a substituent, provided that R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁴ and R²⁵, R²⁵ and R²⁶, R²⁶ and R²⁷, R²⁷ and R²⁸, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R^(3a) and R^(3b), R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁵ and R⁶⁶, R⁶⁶ and R⁶⁷, and R⁶ and R⁶⁸ each may be bonded to each other to form a cyclic structure.

(2) The compound according to the item (1), wherein in the general formula (261), at least one of R³ and R⁶ represents a group represented by any of the general formulae (262) to (266).

(3) The compound according to the item (2), wherein in the general formula (261), R³ and R⁶ each represent a group represented by any of the general formulae (262) to (266).

(4) The compound according to the item (2), wherein in the general formula (261), at least one of R³ and R⁶ represents a group represented by the general formula (263).

(5) The compound according to the item (2), wherein in the general formula (261), at least one of R³ and R⁶ represents a group represented by the general formula (262).

(6) The compound according to any one of the items (1) to (5), wherein in the general formulae (262) to (266), at least one of R²¹ to R²⁸, R³¹ to R³⁸, R⁴¹ to R⁴⁸, R⁵¹ to R⁵⁸, and R⁶¹ to R⁶⁸ represents a substituent.

(7) The compound according to the item (6), wherein in the general formulae (262) to (266), at least one of R²³, R²⁶, R³³, R³⁶, R⁴³, R⁴⁶, R⁵³, R⁵⁶, R⁶³, and R⁶⁶ represents a substituent.

(8) The compound according to the item (7), wherein the substituent is a group represented by any of general formulae (262) to (266).

(9) The compound according to any one of the items (1) to (8), wherein in the general formulae (262) to (266), L represents a single bond.

(10) The compound according to any one of the items (1) to (9), wherein in the general formula (261), X represents an oxygen atom.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (271):

wherein in the general formula (271), R¹ to R¹⁰ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R¹⁰ each independently represent a group represented by the following general formula (272), and R¹ and R², R² and R³, R³ and R⁴, R⁴ and R⁵, R⁶ and R⁷, R⁷ and R⁸, R⁸ and R⁹, and R⁹ and R¹⁰ each may be bonded to each other to form a cyclic structure:

wherein in the general formula (272), R¹¹ to R²⁰ each independently represent a hydrogen atom or a substituent, in which R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, and R¹⁹ and R²⁰ each may be bonded to each other to form a cyclic structure; Ph represents a substituted or unsubstituted phenylene group; and n1 represents 0 or 1.

(2) The compound according to the item (1), wherein the group represented by the general formula (272) is a group represented by any one of the following general formulae (273) to (278):

wherein in the general formulae (273) to (278), R²¹ to R²⁴, R²⁷ to R³⁸, R⁴¹ to R⁴⁸, R⁵¹ to R⁵⁸, R⁶¹ to R⁶⁵, R⁷¹ to R⁷⁹, and R⁸¹ to R⁹⁰ each independently represent a hydrogen atom or a substituent, in which R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁷ and R²⁸, R²⁸ and R²⁹, R²⁹ and R³⁰, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁴ and R⁶⁵, R⁵⁴ and R⁶¹, R⁵⁵ and R⁶⁵, R⁷¹ and R⁷², R⁷² and R⁷³, R⁷³ and R⁷⁴, R⁷⁴ and R⁷⁵, R⁷⁶ and R⁷⁷, R⁷⁷ and R⁷⁸, R⁷⁸ and R⁷⁹, R⁸¹ and R⁸², R⁸² and R⁸³, R⁸³ and R⁸⁴, R⁸⁵ and R⁸⁶, R⁸⁶ and R⁸⁷, R⁸⁷ and R⁸⁸, and R⁸⁹ and R⁹⁰ each may be bonded to each other to form a cyclic structure; Ph represents a substituted or unsubstituted phenylene group; and n1 represents 0 or 1.

(3) The compound according to the item (1) or (2), wherein in the general formula (271), at least one of R¹ to R⁵ and at least one of R⁶ to R¹⁰ each represent a group represented by the general formula (272).

(4) The compound according to the item (3), wherein in the general formula (271), R³ and R⁸ each represent a group represented by the general formula (272).

(5) The compound according to any one of the items (1) to (4), wherein the group represented by the general formula (272) is a group represented by the general formula (274).

(6) The compound according to any one of the items (1) to (4), wherein the group represented by the general formula (272) is a group represented by the general formula (273).

(7) The compound according to the item (6), wherein in the general formula (273), at least one of R²¹ to R²⁴ and R²⁷ to R³⁰ represents a substituent.

(8) The compound according to the item (7), wherein the substituent is a group represented by any one of the general formulae (273) to (278).

(9) The compound according to the item (8), wherein in the general formula (273), at least one of R²³ and R²⁸ represents the substituent.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (281):

wherein in the general formula (281), X represents an oxygen atom or a sulfur atom; R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a group represented by any one of the following general formulae (282) to (287), and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R⁸ and R⁹, and R⁹ and R¹ may be bonded to each other to form a cyclic structure; and R⁹ represents a substituent, provided that when R⁹ contains an atom that contains a lone electron pair without forming a single bond to the boron atom, the atom may form a cyclic structure through a coordination bond with the boron atom:

wherein in the general formulae (282) to (287), L¹² to L¹⁷ each independently represent a single bond or a divalent linking group; * represents the position bonded to the benzene ring in the general formula (281); and R¹¹ to R²⁰, R²¹ to R²⁸, R³¹ to R³, R^(3a), R^(3b), R⁴¹ to R⁴⁸, R^(4a), R⁵¹ to R⁵⁸, R⁶¹ to R⁶⁸ each independently represent a hydrogen atom or a substituent, in which R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ and R²⁰, R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁴ and R²⁵, R²⁵ and R²⁶, R²⁶ and R²⁷, R²⁷ and R²⁸, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R^(3a) and R^(3b), R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁵ and R⁶⁶, R⁶⁶ and R⁶⁷, and R⁶⁷ and R⁶⁸ each may be bonded to each other to form a cyclic structure.

(2) The compound according to the item (1), wherein in the general formula (281), at least one of R¹ to R⁸ represents a group represented by any one of the general formulae (283) to (287).

(3) The compound according to the item (1) or (2), wherein in the case where at least one of R¹ to R⁸ in the general formula (281) represents a group represented by the general formula (283), at least one of R²¹ to R²⁸ in the general formula (283) represents a substituent.

(4) The compound according to any one of the items (1) to (3), wherein in the general formula (281), at least one of R², R³, R⁶, and R⁷ represents a group represented by any one of the general formulae (282) to (287).

(5) The compound according to the item (4), wherein in the general formula (281), at least one of R³ and R⁶ represents a group represented by any one of the general formulae (282) to (287).

(6) The compound according to the item (5), wherein in the general formula (281), R³ and R⁶ each independently represent a group represented by any one of the general formulae (282) to (287).

(7) The compound according to any one of the items (1) to (6), wherein at least one of R¹¹ to R²⁰ in the general formula (282), at least one of R²¹ to R²⁸ in the general formula (283), at least one of R³¹ to R³⁸ and at least one of R^(3a) and R^(3b) in the general formula (284), at least one of R⁴¹ to R⁴⁸ in the general formula (285), at least one of R⁵¹ to R^(5s) in the general formula (286), and at least one of R⁶¹ to R⁶⁸ in the general formula (287) each represent a substituent.

(8) The compound according to the item (7), wherein at least one of R¹³ and R¹⁸ in the general formula (282), at least one of R²³ and R²⁶ in the general formula (283), at least one of R³³ and R³⁶ and at least one of R^(3a) and R^(3b) in the general formula (284), at least one of R⁴³ and R⁴⁶ in the general formula (285), at least one of R⁵³ and R⁵⁶ in the general formula (286), and at least one of R⁶³ and R⁶⁶ in the general formula (287) each represent a substituent.

(9) The compound according to the item (8), wherein at least one of R¹³ and R¹⁸ in the general formula (282), at least one of R²³ and R²⁶ in the general formula (283), at least one of R³³ and R³⁶ and at least one of R^(3a) and R^(3b) in the general formula (284), at least one of R⁴³ and R⁴⁶ in the general formula (285), at least one of R⁵³ and R⁵⁶ in the general formula (286), and at least one of R⁶³ and R⁶⁶ in the general formula (287) each represent a group represented by any one of the general formulae (282) to (287).

(10) The compound according to any one of the items (1) to (9), wherein in the general formulae (282) to (287), L¹² to L¹⁷ each represent a single bond.

(11) The compound according to any one of the items (1) to (10), wherein in the general formula (281), X represents an oxygen atom.

(12) The compound according to any one of the items (1) to (11), wherein in the general formula (281), R⁹ represents a group represented by the following general formula (a):

wherein in the general formula (a), * represents the position bonded to the boron atom in the general formula (281); and R^(9a), R^(9b), R^(9c), R^(9d), and R^(9e) each independently represent a hydrogen atom or a substituent, in which R^(9a) and R^(9b), R^(9b) and R^(9c), R^(9C) and R^(9d), and R^(9d) and R^(9e) may be bonded to each other to form a cyclic structure.

(13) The compound according to the item (12), wherein in the general formula (a), R^(9a) and R^(9e) each represent a substituent.

(14) The compound according to any one of the items (1) to (13), wherein in the general formula (281), at least one of R¹ to R⁸ represents a group represented by the general formula (284).

(15) The compound according to any one of the items (1) to (4), and (7) to (14), wherein in the general formula (281), R³ and R⁶, or R² and R⁷ each represent a group represented by the general formula (284).

(16) The compound according to the item (14) or (15), wherein in the general formula (284), R^(3a) and R^(3b) each represent a substituent.

(17) The compound according to any one of the items (14) to (16), wherein the substituent is an alkyl group having from 1 to 15 carbon atoms or a phenyl group.

(18) The compound according to any one of the items (14) to (16), wherein in the general formula (284), R^(3a) and R^(3b) are bonded to each other to form a cyclic structure.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (291):

wherein in the general formula (291), X represents O, S, N—R¹¹, C═O, C(R¹²) (R¹³), or Si(R¹⁴)(R¹⁵); Y represents O, S, or N—R¹⁶; Ar¹ represents a substituted or unsubstituted arylene group; Ar² represents an aromatic ring or a heteroaromatic ring; and R¹ to R⁸ and R¹¹ to R¹⁶ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each may be bonded to each other to form a cyclic structure.

(2) The compound according to the item (1), wherein the compound represented by the general formula (291) is a compound represented by the following general formula (292):

wherein in the general formula (292), X represents O, S, N—R¹¹, C═O, C(R¹²) (R¹³), or Si(R¹⁴) (R¹⁵); Y represents O, S, or N—R¹⁶; Ar² represents an aromatic ring or a heteroaromatic ring; and R¹ to R⁸, R¹¹ to R¹⁶, and R²¹ to R²⁴ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R²¹ and R²², and R²³ and R²⁴ each may be bonded to each other to form a cyclic structure.

(3) The compound according to the item (1), wherein the compound represented by the general formula (291) is a compound represented by the following general formula (293):

wherein in the general formula (293), X represents O, S, N—R¹¹, C═O, C(R¹²) (R¹³), or Si(R¹⁴) (R¹⁵); Y represents O, S, or N—R¹⁶; and R¹ to R⁸, R¹¹ to R¹⁶, R²¹ to R²⁴, and R³¹ to R³⁴ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R²¹ and R²², R²³ and R²⁴, R³¹ and R³², R³² and R³³, and R³³ and R³⁴ each may be bonded to each other to form a cyclic structure.

(4) The compound according to any one of the items (1) to (3), wherein X represents O or S.

(5) The compound according to any one of the items (1) to (4), wherein Y represents O, S, or N—R¹⁶, and R¹⁶ represents a substituted or unsubstituted aryl group.

(6) The compound according to any one of the items (1) to (5), wherein R¹ to R⁸ each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 10 carbon atoms, a substituted or unsubstituted dialkylamino group having from 1 to 10 carbon atoms, a substituted or unsubstituted diarylamino group having from 12 to 40 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 12 carbon atoms.

Examples of the compound include the following compounds.

Examples of the preferred light-emitting material include the following compounds.

(1) A compound represented by the following general formula (301): (D)_(n)-A  General Formula (301) wherein in the general formula (301), D represents a group represented by the following general formula (302); A represents an n-valent group containing a structure represented by the following general formula (303); and n represents an integer of from 1 to 8:

wherein in t e genera formula (302), Z¹ represents O, S, C═O, C(R²¹) (R²²), Si(R²³) (R²⁴), N—Ar³, or a single bond; R²¹ to R²⁴ each independently represent an alkyl group having from 1 to 8 carbon atoms; Ar³ represents a substituted or unsubstituted aryl group; and R¹ to R⁸ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ may be bonded to each other to form a cyclic structure, and when Z¹ represents a single bond, at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group:

wherein in the general formula (303), Y represents O, S, or N—Ar⁴; and Ar⁴ represents a substituted or unsubstituted aryl group.

(2) The compound according to the item (1), wherein in the general formula (302), Z¹ represents O, S, C═O, C(R²¹) (R²²), Si(R²³) (R²⁴), or a single bond.

(3) The compound according to the item (1), wherein in the general formula (302), Z¹ represents N—Ar³.

(4) The compound according to any one of the items (1) to (3), wherein in the general formula (301), A has a structure represented by the following general formula (304):

wherein in the general formula (304), Y represents O, S, or N—Ar⁴; and Ar¹ and Ar² each independently represent a substituted or unsubstituted aromatic group.

(5) The compound according to any one of the items (1) to (4), wherein in the general formula (301), n represents an integer of from 1 to 4.

(6) The compound according to any one of the items (1) to (3), wherein the compound is represented by the following general formula (305):

wherein in the general formula (305), Z¹ and Z² each independently represent O, S, C═O, C(R²¹) (R²²), Si(R²³) (R²⁴), N—Ar³, or a single bond; R²¹ to R²⁴ each independently represent an alkyl group having from 1 to 8 carbon atoms; Ar³ represents a substituted or unsubstituted aryl group; Ar¹ and Ar² each independently represent a substituted or unsubstituted aromatic group; Y represents O, S, or N—Ar⁴; Ar⁴ represents a substituted or unsubstituted aryl group; R¹ to R⁸ and R¹¹ to R¹⁸ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, and R¹⁷, and R¹⁸ each may be bonded to each other to form a cyclic structure, provided that when Z¹ represents a single bond, at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group, and when Z² represents a single bond, at least one of R¹¹ to R¹⁸ represents a substituted or unsubstituted diarylamino group; and n1 and n2 each independently represent an integer of from 0 to 8, provided that the sum of n1 and n2 is from 1 to 8.

(7) The compound according to the item (6), wherein in the general formula (305), Z¹ and Z² each independently represent O, S, N—Ar³, or a single bond.

(8) The compound according to the item (6) or (7), wherein in the general formula (305), Y represents 0 or N—Ar⁴.

(9) The compound according to any one of the items (1) to (3), wherein the compound is represented by the following general formula (306):

wherein in the general formula (306), Z¹ represents O, S, C═O, C(R²¹) (R²²), Si(R²³) (R²⁴), N—Ar³, or a single bond; R²¹ to R²⁴ each independently represent an alkyl group having from 1 to 8 carbon atoms; Ar³ represents a substituted or unsubstituted aryl group; Ar^(1′) represents a substituted or unsubstituted arylene group; Ar^(2′) represents a substituted or unsubstituted aryl group; Y represents O, S, or N—Ar⁴; Ar⁴ represents a substituted or unsubstituted aryl group; and R¹ to R⁸ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each may be bonded to each other to form a cyclic structure, provided that when Z¹ represents a single bond, at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group.

(10) The compound according to any one of the items (1) to (3), wherein the compound is represented by the following general formula (307):

wherein in the general formula (307), Z¹ and Z² each independently represent O, S, C═O, C(R²¹) (R²²), Si(R²³) (R²⁴), N—Ar³, or a single bond; R²¹ to R²⁴ each independently represent an alkyl group having from 1 to 8 carbon atoms; Ar³ represents a substituted or unsubstituted aryl group; Ar^(1″) and Ar^(2″) each independently represent a substituted or unsubstituted arylene group; Y represents O, S, or N—Ar⁴; Ar⁴ represents a substituted or unsubstituted aryl group; and R¹ to R⁸ and R¹¹ to R¹⁸ each independently represent a hydrogen atom or a substituent, in which R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, and R¹⁷ and R¹⁸ each may be bonded to each other to form a cyclic structure, provided that when Z¹ represents a single bond, at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group, and when Z² represents a single bond, at least one of R¹¹ to R¹⁸ represents a substituted or unsubstituted diarylamino group.

(11) The compound according to the item (10), wherein in the general formula (307), Z¹ and Z² are the same as each other, Ar^(1″) and Ar^(2″) are the same as each other, R¹ and R¹⁴ are the same as each other, R² and R¹³ are the same as each other, R³ and R¹² are the same as each other, R⁴ and R¹¹ are the same as each other, R⁵ and R¹⁸ are the same as each other, R⁶ and R¹⁷ are the same as each other, R⁷ and R¹⁶ are the same as each other, and R⁸ and R¹⁵ are the same as each other.

(12) The compound according to the item (10) or (11), wherein in the general formula (307), Z¹ and Z² each independently represent O, S, or N—Ar³.

Examples of the compound include the following compounds.

In the case where the compound represented by the general formula (1) is used as a light-emitting material, on the other hand, one kind or two or more kinds selected from the group of compounds represented by the general formula (1) of the invention may be used therefor. As described above, from the standpoint that the singlet excitons and the triplet excitons generated in the light-emitting material are confined in the light-emitting material, a host material is preferably used in addition to the light-emitting material in the light-emitting layer. The host material used may be an organic compound that has excited singlet energy and excited triplet energy, at least one of which is higher than those of the light-emitting material of the invention. Even though the singlet excitons and the triplet excitons are not confined sufficiently, however, a high light emission efficiency may be obtained in some cases, and thus a host material that is capable of achieving a high light emission efficiency may be used in the invention without any particular limitation.

In the organic light-emitting device and the organic electroluminescent device of the invention, the light emission occurs in the light-emitting material of the invention contained in the light-emitting layer. The emitted light contains both fluorescent light and delayed fluorescent light. However, a part of the emitted light may contain emitted light from the host material, or the emitted light may partially contain emitted light from the host material.

In the case where the host material is used, the amount of the compound of the invention as the light-emitting material contained in the light-emitting layer is preferably 0.1% by weight or more, and more preferably 1% by weight or more, and is preferably 50% by weight or less, more preferably 20% by weight or less, and further preferably 10% by weight or less. The host material in the light-emitting layer is preferably an organic compound that has a hole transporting function and an electron transporting function, prevents the emitted light from being increased in wavelength, and has a high glass transition temperature.

Injection Layer

The injection layer is a layer that is provided between the electrode and the organic layer, for decreasing the driving voltage and enhancing the light emission luminance, and includes a hole injection layer and an electron injection layer, which may be provided between the anode and the light-emitting layer or the hole transporting layer and between the cathode and the light-emitting layer or the electron transporting layer. The injection layer may be provided depending on necessity.

Barrier Layer

The barrier layer is a layer that is capable of inhibiting charges (electrons or holes) and/or excitons present in the light-emitting layer from being diffused outside the light-emitting layer. The electron barrier layer may be disposed between the light-emitting layer and the hole transporting layer, and inhibits electrons from passing through the light-emitting layer toward the hole transporting layer. Similarly, the hole barrier layer may be disposed between the light-emitting layer and the electron transporting layer, and inhibits holes from passing through the light-emitting layer toward the electron transporting layer. The barrier layer may also be used for inhibiting excitons from being diffused outside the light-emitting layer. Thus, the electron barrier layer and the hole barrier layer each may also have a function as an exciton barrier layer. The term “the electron barrier layer” or “the exciton barrier layer” referred herein is intended to include a layer that has both the functions of an electron barrier layer and an exciton barrier layer by one layer.

Hole Barrier Layer

The hole barrier layer has the function of an electron transporting layer in a broad sense. The hole barrier layer has a function of inhibiting holes from reaching the electron transporting layer while transporting electrons, and thereby enhances the recombination probability of electrons and holes in the light-emitting layer. As the material for the hole barrier layer, the materials for the electron transporting layer described later may be used depending on necessity.

Electron Barrier Layer

The electron barrier layer has the function of transporting holes in abroad sense. The electron barrier layer has a function of inhibiting electrons from reaching the hole transporting layer while transporting holes, and thereby enhances the recombination probability of electrons and holes in the light-emitting layer.

Exciton Barrier Layer

The exciton barrier layer is a layer for inhibiting excitons generated through recombination of holes and electrons in the light-emitting layer from being diffused to the charge transporting layer, and the use of the layer inserted enables effective confinement of excitons in the light-emitting layer, and thereby enhances the light emission efficiency of the device. The exciton barrier layer may be inserted adjacent to the light-emitting layer on any of the side of the anode and the side of the cathode, and on both the sides. Specifically, in the case where the exciton barrier layer is present on the side of the anode, the layer may be inserted between the hole transporting layer and the light-emitting layer and adjacent to the light-emitting layer, and in the case where the layer is inserted on the side of the cathode, the layer may be inserted between the light-emitting layer and the cathode and adjacent to the light-emitting layer. Between the anode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the anode, a hole injection layer, an electron barrier layer and the like may be provided, and between the cathode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the cathode, an electron injection layer, an electron transporting layer, a hole barrier layer and the like may be provided. In the case where the barrier layer is provided, the material used for the barrier layer preferably has excited singlet energy and excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy of the light-emitting layer, respectively.

Hole Transporting Layer

The hole transporting layer is formed of a hole transporting material having a function of transporting holes, and the hole transporting layer may be provided as a single layer or plural layers.

The hole transporting material has one of injection or transporting property of holes and barrier property of electrons, and may be any of an organic material and an inorganic material. Examples of known hole transporting materials that may be used herein include a triazole derivative, an oxadiazole derivative, an imidazole derivative, a carbazole derivative, an indolocarbazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, an oxazole derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aniline copolymer and an electroconductive polymer oligomer, particularly a thiophene oligomer. Among these, a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound are preferably used, and an aromatic tertiary amine compound is more preferably used.

Electron Transporting Layer

The electron transporting layer is formed of a material having a function of transporting electrons, and the electron transporting layer may be provided as a single layer or plural layers.

The electron transporting material (which may also function as a hole barrier material in some cases) needs only to have a function of transporting electrons, which are injected from the cathode, to the light-emitting layer. Examples of the electron transporting layer that may be used herein include a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyran dioxide derivative, carbodiimide, a fluorenylidene methane derivative, anthraquinodimethane and anthrone derivatives, and an oxadiazole derivative. The electron transporting material used may be a thiadiazole derivative obtained by replacing the oxygen atom of the oxadiazole ring of the oxadiazole derivative by a sulfur atom, or a quinoxaline derivative having a quinoxaline ring, which is known as an electron withdrawing group. Furthermore, polymer materials having these materials introduced to the polymer chain or having these materials used as the main chain of the polymer may also be used.

In the production of the organic electroluminescent device, the compound represented by the general formula (1) may be used not only in the light-emitting layer but also in the other layers than the light-emitting layer. In this case, the compound represented by the general formula (1) used in the light-emitting layer and the compound represented by the general formula (1) used in the other layers than the light-emitting layer may be the same as or different from each other. For example, the compound represented by the general formula (1) may be used in the injection layer, the barrier layer, the hole barrier layer, the electron barrier layer, the exciton barrier layer, the hole transporting layer, the electron transporting layer and the like described above. The film forming method of the layers are not particularly limited, and the layers may be produced by any of a dry process and a wet process.

Specific examples of preferred materials that may be used in the organic electroluminescent device are shown below, but the materials that may be used in the invention are not construed as being limited to the example compounds. The compound that is shown as a material having a particular function may also be used as a material having another function. In the structural formulae of the example compounds, R and R₂ to R₇ each independently represent a hydrogen atom or a substituent, and n represents an integer of from 3 to 5.

In the case where the compound represented by the general formula (1) is used as a light-emitting material, preferred examples of a compound that may also be used as the host material of the light-emitting layer are shown below.

Preferred examples of a compound that may be used as the hole injection material are shown below.

Preferred examples of a compound that may be used as the hole transporting material are shown below.

Preferred examples of a compound that may be used as the electron barrier material are shown below.

Preferred examples of a compound that may be used as the hole barrier material are shown below.

Preferred examples of a compound that may be used as the electron transporting material are shown below.

Preferred examples of a compound that may be used as the electron injection material are shown below.

Preferred examples of a compound as a material that may be added are shown below. For example, the compound may be added as a stabilizing material.

The organic electroluminescent device thus produced by the aforementioned method emits light on application of an electric field between the anode and the cathode of the device. In this case, when the light emission is caused by the excited singlet energy, light having a wavelength that corresponds to the energy level thereof may be confirmed as fluorescent light and delayed fluorescent light. When the light emission is caused by the excited triplet energy, light having a wavelength that corresponds to the energy level thereof may be confirmed as phosphorescent light. The normal fluorescent light has a shorter light emission lifetime than the delayed fluorescent light, and thus the light emission lifetime may be distinguished between the fluorescent light and the delayed fluorescent light.

The phosphorescent light may substantially not observed with a normal organic compound, such as the compound of the invention, at room temperature since the excited triplet energy is converted to heat or the like due to the instability thereof, and is immediately deactivated with a short lifetime. The excited triplet energy of the normal organic compound may be measured by observing light emission under an extremely low temperature condition.

The organic electroluminescent device of the invention may be applied to any of a single device, a structure with plural devices disposed in an array, and a structure having anodes and cathodes disposed in an X-Y matrix. According to the invention, an organic light-emitting device that is largely improved in light emission efficiency may be obtained by adding the compound represented by the general formula (1) in the light-emitting layer. The organic light-emitting device, such as the organic electroluminescent device, of the invention may be applied to a further wide range of purposes. For example, an organic electroluminescent display apparatus may be produced with the organic electroluminescent device of the invention, and for the details thereof, reference may be made to S. Tokito, C. Adachi and H. Murata, “Yuki EL Display” (Organic EL Display) (Ohmsha, Ltd.). In particular, the organic electroluminescent device of the invention may be applied to organic electroluminescent illumination and backlight which are highly demanded.

EXAMPLE

The features of the invention will be described more specifically with reference to synthesis examples and working examples below. The materials, processes, procedures and the like shown below may be appropriately modified unless they deviate from the substance of the invention. Accordingly, the scope of the invention is not construed as being limited to the specific examples shown below. The light emission characteristics were evaluated by using a source meter (2400 Series, produced by Keithley Instruments Inc.), a semiconductor parameter analyzer (E5273A, produced by Agilent Technologies, Inc.), an optical power meter (1930C, produced by Newport Corporation), an optical spectrometer (USB2000, produced by Ocean Optics, Inc.), a spectroradiometer (SR-3, produced by Topcon Corporation), and a streak camera (Model C4334, produced by Hamamatsu Photonics K.K.).

Synthesis Example 1 Synthesis of Compound 1

m-Carborane (1.87 g, 13.0 mmol) was placed in a three-neck flask, which was then replaced by nitrogen. Thereafter, 80 mL of tetrahydrofuran was added thereto, the mixture was cooled to −78° C., and a 1.60 M n-butyllithium hexane solution (9.80 mL, 26.0 mmol) was slowly added dropwise thereto, followed by agitating at −78° C. for 15 minutes. Thereafter, the mixture was agitated at 0° C. for 1 hour, and copper (I) chloride (1.39 g, 14.3 mmol) was added thereto, followed by agitating at room temperature for 30 minutes. Thereafter, 100 mL of a tetrahydrofuran solution containing palladium(II) acetate (0.15 g, 0.676 mmol), trismethoxytriphenylphosphine (0.75 g, 2.13 mmol), and 9-(4-bromophenyl)carbazole (5.00 g, 15.6 mmol) was added, followed by agitating at room temperature for 48 hours. Thereafter, water and chloroform were added to the mixture, which was extracted therewith. The organic layer separated was dried over sodium sulfate, and suction-filtered to provide a filtrate. The resulting filtrate was purified by column chromatography and recrystallization, thereby providing 1-(4-carbazol-9-ylphenyl)-m-carborane (yield: 37.1%).

1-(4-Carbazolylphenyl)-m-carborane (1.56 g, 4.0 mmol) was placed in a three-neck flask, which was then replaced by nitrogen. Thereafter, 80 mL of tetrahydrofuran was added thereto, the mixture was cooled to −78° C., and a 1.60 M n-butyllithium hexane solution (5.0 mL, 8.0 mmol) was slowly added dropwise thereto, followed by agitating at −78° C. for 15 minutes. Thereafter, the mixture was agitated at 0° C. for 1 hour, and copper(I) chloride (0.52 g, 5.2 mmol) was added thereto, followed by agitating at room temperature for 30 minutes. Thereafter, 100 mL of a tetrahydrofuran solution containing palladium(II) acetate (0.047 g, 0.208 mmol), trismethoxytriphenylphosphine (0.23 g, 0.656 mmol), and 2-chloro-4,6-diphenyl-1,3,5-triazine (1.3 g, 4.8 mmol) was added, followed by agitating at room temperature for 48 hours. Thereafter, water and chloroform were added to the mixture, which was extracted therewith. The organic layer separated was dried over sodium sulfate, and suction-filtered to provide a filtrate. The resulting filtrate was purified by column chromatography, thereby providing the compound 1 (yield: 44.5%) The compound was identified by ¹H-NMR and elemental analysis.

¹H-NMR (500 MHz, CDCl₃, TMS, δ): 8.68 (d, J=7.0 Hz, 4H), 8.14 (d, J=7.5 Hz, 2H), 7.77 (d, J=8.5 Hz, 2H), 7.65-7.62 (m, 2H), 7.58-7.53 (m, 6H), 7.47-7.40 (m, 4H) 7.30 (t, J=9.0 Hz, 2H), 3.89-1.75 (br, 10H, B—H)

Elemental analysis: Anal. Calcd. for C₃₅H₃₂B₁₀N₄: C, 68.16%; H, 5.23%; N, 9.08%; found: C, 68.25%; H, 5.21%; N, 9.17%.

Synthesis Example 2 Synthesis of Compound 2

1-(4-Carbazolylphenyl)-m-carborane (1.56 g, 4.0 mmol) was placed in a three-neck flask, which was then replaced by nitrogen. Thereafter, 80 mL of tetrahydrofuran was added thereto, the mixture was cooled to −78° C., and a 1.60 M n-butyllithium hexane solution (5.0 mL, 8.0 mmol) was slowly added dropwise thereto, followed by agitating at −78° C. for 15 minutes. Thereafter, the mixture was agitated at 0° C. for 1 hour, and copper(I) chloride (0.52 g, 5.2 mmol) was added thereto, followed by agitating at room temperature for 30 minutes. Thereafter, 100 mL of a tetrahydrofuran solution containing palladium(II) acetate (0.047 g, 0.208 mmol), trismethoxytriphenylphosphine (0.23 g, 0.656 mmol), and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (1.86 g, 4.8 mmol) was added, followed by agitating at room temperature for 48 hours. Thereafter, water and chloroform were added to the mixture, which was extracted therewith. The organic layer separated was dried over sodium sulfate, and suction-filtered to provide a filtrate. The resulting filtrate was purified by column chromatography, thereby providing the compound 2 (yield: 10.8%). The compound was identified by 1H-NMR and elemental analysis.

¹H-NMR (500 MHz, CDCl₃, TMS, δ): 8.77 (d, J=9.7 Hz, 4H), 8.69 (d, J=8.7 Hz, 2H), 8.14 (d, J=7.7 Hz, 2H), 7.75-7.72 (m, 4H), 7.65-7.57 (m, 6H), 7.53 (d, J=8.7 Hz, 2H), 7.47-7.40 (m, 4H), 6.5 (t, J=8.7 Hz, 2H), 3.80-1.76 (br, 11H, B—H)

Synthesis Example 3 Synthesis of Compound 3

9-(4-Ethynylphenyl)-9H-carbazole (2.13 g, 8.0 mmol) and brominated triphenyltriazine (2.06 g, 5.3 mmol) were placed in a three-neck flask, which was then replaced by nitrogen. Thereafter, 180 mL of triethylamine and 100 mL of tetrahydrofuran were added thereto for dissolution, and then tetrakis(triphenylphosphine) palladium(0) (0.31 g, 0.0266 mmol) and copper(I) iodide (0.05 g, 5.57 mmol) were added, followed by refluxing for 24 hours. Thereafter, water and chloroform were added to the mixture, which was extracted therewith. The organic layer separated was dried over sodium sulfate, and suction-filtered to provide a filtrate. The resulting filtrate was purified by column chromatography, thereby providing 9-(4-((4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)ethynyl)phenyl)-9H-carbazole (yield: 39.3%).

Decaborane (0.234 g, 1.91 mmol) and N,N-dimethylaniline (0.580 g, 4.79 mmol) were placed in a 100 mL three-neck flask having been replaced by nitrogen, and dissolved with 50 mL of toluene. The solution was agitated at room temperature for 30 minutes, and then heated for refluxing under agitating for 2 hours. Thereafter, the temperature thereof was lowered to 40° C., to which 9-(4-((4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)ethynyl)phenyl)-9H-carbazole (1.0 g, 1.74 mmol) was added, followed by refluxing for 24 hours. Thereafter, water and chloroform were added to the mixture, which was extracted therewith. The organic layer separated was dried over sodium sulfate, and suction-filtered to provide a filtrate. A solid was obtained by reprecipitation and purified by sublimation, thereby providing the compound 3 (yield: 21.8%). The compound was identified by ¹H-NMR and elemental analysis. ¹H-NMR (500 MHz, CDCl₃, TMS, δ): 8.72 (d, J=8.5 Hz, 4H), 8.64 (d, J=8.5 Hz, 2H), 8.02 (d, J=7.5 Hz, 2H), 7.72-7.69 (m, 4H), 7.63-7.54 (m, 6H), 7.39 (d, J=8.5 Hz, 2H), 7.24-7.14 (m, 6H), 3.83-1.78 (br, 10H, B—H)

Example 1

Production and Evaluation of Organic Photoluminescent Device Using Compound 1 as Host Material

A light-emitting material containing 4CzIPN, and the compound 1 were vapor-deposited from separate vapor deposition sources on a quartz substrate by a vacuum vapor deposition method under condition of a vacuum degree of from 2 to 7.0×10⁻⁴ Pa, so as to form a thin film having a concentration of 4CzIPN of 3.0% by weight to a thickness of 100 nm, thereby providing an organic photoluminescent device.

FIG. 2 shows the light emission and absorption spectra of the organic photoluminescent device thus produced with excitation light of 280 nm. The photoluminescence quantum efficiency was 84.9%.

Example 2

Production and Evaluation of Organic Electroluminescent Device Using Compound 1 as Host Material

Thin films were laminated on a glass substrate having formed thereon an anode formed of indium tin oxide (ITO) having a thickness of 100 nm, by a vacuum vapor deposition method at a vacuum degree of from 2 to 7.0×10⁻⁴ Pa. Firstly, α-NPD was formed to a thickness of 35 nm on ITO, and then mCP was formed to a thickness of 10 nm thereon. Subsequently, a light-emitting material containing 4CzIPN and the compound 1 were co-deposited thereon from separate vapor deposition sources to form a layer having a thickness of 20 nm, which was designated as a light-emitting layer. At this time, the concentration of 4CzIPN was 3.0% by weight. PPT was then formed to a thickness of 40 nm, further lithium fluoride (LiF) was vacuum vapor-deposited to a thickness of 0.8 nm, and then aluminum (Al) was vapor-deposited to a thickness of 80 nm to form a cathode, thereby completing an organic electroluminescent device.

FIG. 3 shows the light emission spectrum of the organic electroluminescent device thus produced at 10 mA/cm², FIG. 4 shows the voltage-current density-luminance characteristics thereof, and FIG. 5 shows current density-external quantum efficiency characteristics thereof. The organic electroluminescent device using the compound 1 as a host material exhibited a voltage of 3.9 V at a light emission wavelength of 501 nm at 1 cd/m², a voltage of 7.6 V at 10 mA/cm², a luminance of 28,980 cd/m² at 10 V, and an external quantum efficiency of 19.4% at 0.01 mA/cm², which indicated a high external quantum efficiency.

Example 3

Production and Evaluation of Organic Photoluminescent Device Using Compound 1 as Light-Emitting Material

Toluene solutions of the compound 1 having a concentrations of 10⁻³ M, 10⁻⁴ M, and 10⁻⁵ M were prepared in a glove box under an Ar atmosphere.

The compound 1 was vapor-deposited on a quartz substrate by a vacuum vapor deposition method under condition of a vacuum degree of from 2 to 7.0×10⁻⁴ Pa to form a thin film of the compound 1 to a thickness of 100 nm, thereby providing an organic photoluminescent device.

The specimens using the compound 1 were measured for light emission and absorption spectra with excitation light of 280 nm. FIG. 6 shows the light emission and absorption spectra of the toluene solutions before bubbling with nitrogen and the organic photoluminescent device measured in the air, and FIG. 7 shows the light emission and absorption spectra of the toluene solutions after bubbling with nitrogen and the thin film organic photoluminescent device measured in a nitrogen-containing atmosphere.

The photoluminescence quantum efficiency of the toluene solution of the compound 1 before bubbling with nitrogen was 1.9% for the toluene solution of 10⁻³ M, 2.1% for the toluene solution of 10⁻⁴ M, and 2.7% for the toluene solution of 10⁻⁵M, and that after bubbling with nitrogen was 76.3% for the toluene solution of 10⁻³ M, 17.8% for the toluene solution of 10⁻⁴ M, and 5.3% for the toluene solution of 10⁻⁵ M. The photoluminescence quantum efficiency of the organic photoluminescent device having the thin film of the compound 1 was 33.9% measured in the air, and 47.0% measured in a nitrogen-containing atmosphere.

FIG. 8 shows the light emission spectra for fluorescent light, delayed fluorescent light, and total fluorescent light of the organic photoluminescent device having the thin film of the compound 1, and FIG. 9 shows the transient decay curve measured at 300 K thereof. The transient decay curve shows the measurement result of the light emission lifetime obtained by measuring the process where the light emission intensity is deactivated on irradiating the compound with excitation light. In ordinary one-component light emission (fluorescent light or phosphorescent light), the light emission intensity is decays monoexponentially. This means that the light emission intensity decays linearly on a graph with the semilogarithm as the ordinate. In a transient decay curve of the compound 1 shown in FIG. 9, while a linear component (fluorescent light) was observed in the initial stage of observation, a component that deviated from the linearity appeared after several microseconds. The later component is light emission of the delayed component, and the signal thereof added to the initial component appears as a long tail curve on the longer time side. Thus, the measurement of the light emission lifetime revealed that the compound 1 was a light-emitting material that contained a delayed component in addition to a fluorescent component.

Example 4

Production and Evaluation of Organic Photoluminescent Device Using Compound 2 as Light-Emitting Material

A toluene solution having a concentration of 10⁻³ mol/L was prepared in the same manner as in Example 3 except that the compound 2 was used instead of the compound 1.

FIG. 10 shows the light emission and absorption spectra of the toluene solution of the compound 2 thus prepared, with excitation light of 320 nm after bubbling with nitrogen. The photoluminescence quantum efficiency was 12.8%.

INDUSTRIAL APPLICABILITY

The compound represented by the general formula (1) is useful as a host material or a light-emitting material. Accordingly, the compound of the invention may be effectively used as a host material or a light-emitting material of an organic light-emitting device, such as an organic electroluminescent device. The compound of the invention includes a compound that emits delayed fluorescent light, and thus may be capable of providing an organic light-emitting device having a high light emission efficiency. Thus, the invention has high industrial applicability.

REFERENCE SIGNS LIST

-   1 substrate -   2 anode -   3 hole injection layer -   4 hole transporting layer -   5 light-emitting layer -   6 electron transporting layer -   7 cathode 

The invention claimed is:
 1. An organic light-emitting device comprising a compound represented by the following general formula (1) in a light-emitting layer:

wherein in the general formula (1), X¹ to X¹² each independently represent C or BH constituting carborane, provided that among X¹ to X¹², the bonding positions to A and D each represent C, and the other thereof each represent BH; A represents an acceptor bonded to the carborane through an aromatic ring or a heteroaromatic ring; and D represents a donor bonded to the carborane through an aromatic ring or a heteroaromatic ring, and the compound represented by the general formula (1) emits light.
 2. The organic light-emitting device according to claim 1, wherein the organic light-emitting device contains the compound represented by the general formula (1) as a host material.
 3. The organic light-emitting device according to claim 2, wherein the light-emitting layer further contains a delayed fluorescent emitter.
 4. The organic light-emitting device according to claim 1, wherein the organic light-emitting device contains the compound represented by the general formula (1) as a light-emitting material.
 5. The organic light-emitting device according to claim 1, wherein in the general formula (1), D is bonded to the carborane through a benzene ring.
 6. The organic light-emitting device according to claim 1, wherein in the general formula (1), D has a diphenylamino group or a carbazolyl group.
 7. The organic light-emitting device according to claim 1, wherein in the general formula (1), D represents a group represented by the following general formula (2): [(R¹)(R²)N]_(n1)—Ar¹—  General Formula (2) wherein in the general formula (2), R¹ and R² each independently represent a substituent, provided that R¹ and R² may be bonded to each other to form a cyclic structure; n1 represents an integer of from 1 to 4; and Ar¹ represents a substituted or unsubstituted aromatic group having a valence of (n1+1).
 8. The organic light-emitting device according to claim 7, wherein in the general formula (2), n1 represents 1 or
 2. 9. The organic light-emitting device according to claim 1, wherein in the general formula (1), A has a heteroaromatic ring containing a nitrogen atom.
 10. The organic light-emitting device according to claim 9, wherein in the general formula (1), A has a triazine ring.
 11. The organic light-emitting device according to claim 10, wherein the triazine ring is substituted with a phenyl group.
 12. The organic light-emitting device according to claim 9, wherein in the general formula (1), A is bonded to the carborane through the heteroaromatic ring containing a nitrogen atom.
 13. The organic light-emitting device according to claim 9, wherein in the general formula (1), A represents a group represented by the following general formula (3): (Het)_(n2)-Ar²—  General Formula (3) wherein in the general formula (3), Het represents a substituted or unsubstituted heteroaromatic ring group (provided that the heteroaromatic ring group contains a nitrogen atom as a ring structure constituting atom); n2 represents an integer of from 1 to 4; and Ar² represents a substituted or unsubstituted aromatic group having a valence of (n2+1).
 14. The organic light-emitting device according to claim 13, wherein in the general formula (3), n2 represents 1 or
 2. 15. The organic light-emitting device according to claim 1, wherein the compound represented by the general formula (1) is an o-carborane compound or a m-carborane compound.
 16. The organic light-emitting device according to claim 1, wherein the organic light-emitting device is an organic electroluminescent device.
 17. The organic light-emitting device according to claim 1, wherein the organic light-emitting device emits delayed fluorescent light. 